Substituted pyridine compounds

ABSTRACT

Compounds of the formula ##SPC1## 
     Wherein X is aliphatic, cycloaliphatic, aromatic, aralkyl, hetaryl, hetarylalkyl or hydrogen; Y is aliphatic, aromatic, aralkyl, --COOR 2 , --COR 2 , ##EQU1## --CN, --NH 2 , --NO, --NO 2  or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z 1  is cyano, ##EQU2## --OR 12 , --SR 12  or --SO 2  R 12  and Z 2  is chlorine, bromine, cyano, hydroxy, mercapto, ##EQU3## R 1  is aliphatic; R 2  is aliphatic, cycloaliphatic, aromatic, aralkyl or heterocyclic; R 3  and R 4  when taken separately are hydrogen, aliphatic, cycloaliphatic, aromatic or aralkyl; R 3  and R 4  when taken together with the nitrogen atom to which they are attached form a heterocyclic moiety; R 5  and R 6  when taken separately are aliphatic, aromatic, aralkyl, heterocyclic or hydrogen; R 5  and R 6  when taken together with the nitrogen atom to which they are attached are heterocyclic; R 7  is hydrogen; aliphatic or aromatic; R 8  and R 9  are aliphatic or aromatic, R 10  is hydrogen, aliphatic or aralkyl, R 11  is aliphatc and R 12  is aliphatic, aromatic or aralkyl; R 10  and R 11  when taken together with the nitrogen atom to which they are attached are heterocyclic.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a division of application Ser. No. 372,024 filed June 21, 1973.

This invention relates to compounds of the formula ##SPC2##

Wherein X is alkyl having 1 to 6 carbon atoms, alkenyl having 2 tp 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, heteroaryl having 4 to 7 carbon atoms and containing one or two heteroatoms selected from the group of O, N and S, phenyl, benzyl, phenethyl, one of said radicals substituted as hereinafter defined or hydrogen; Y is alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl, benzyl, phenethyl, one of said radicals substituted as hereinafter defined, --COOR₁, --COR₂, ##EQU4## --CN, --NH₂, --NO, --NO₂ or hydrogen with the proviso that when Y is hydrogen, X is other than hydrogen; Z₁ is cyano, ##EQU5## --OR₁₂, --SR₁₂ or --SO₂ R₁₂ and Z₂ is chlorine, bromine, cyano, hydroxy, mercapto, --OR₁₂, --SR₁₂, --SO₂ R₁₂, ##EQU6## R₁ is alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms or one of said radicals substituted as hereinafter defined; R₂ is alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl, benzyl, phenethyl, pyridyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, thienyl, furyl or pyrrolyl, one of said radicals substituted as hereinafter defined; R₃ and R₄, when taken separately, are alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl, benzyl, phenethyl, one of said radicals substituted as hereinafter defined or hydrogen; R₃ and R₄, when taken together with the nitrogen atom to which they are attached, form a piperidino, piperazino, morpholino, or ethyleneimino radical; R₅ and R₆, when taken separately, are alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl benzyl, phenethyl, pyridyl, thi-azolyl, benzothiazolyl, imidazolyl, bemzimidazolyl, pyrrolyl, one of said radicals substituted as hereinafter defined or hydrogen; R₅ and R₆ when taken together with the nitrogen atom to which they are attached, form a piperidino, piperazino, morpholino or ethyleneimino radical; R₇ is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl or phenyl substituted as hereinafter defined; R₈ and R₉ are alkyl having 1 to 6 carbon atoms, phenyl or phenyl substituted as hereinafter defined; R₁₀ is alkyl having 1 to 6 carbon atoms, benzyl, phenethyl, one of said groups substituted as hereinafter defined or hydrogen; R₁₁ is alkyl having 1 to 6 carbon atoms or said alkyl substituted as hereinafter defined; R₁₂ is alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl, benzyl, phenethyl or one of said radicals substituted as hereinafter defined; the substituents for substituted alkyl or alkenyl radicals specified hereinabove being selected from the group consisting of cyano, hydroxy, acetoxy, phenoxyacetoxy, alkoxy having 1 to 2 carbon atoms, phenoxy, monoalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, N-ethylcarbamoyloxy, N-methylcarbamoyloxy, N-phenylcarbamoyloxy, acetylamino, benzoylamino, heteroaryl having 4 to 7 carbon atoms and containing one or two heteroatoms selected from the group of O, N and S, and ##EQU7## wherein Z constitutes the atoms completing a morpholino, piperidino, piperazino, N-methyl-piperazino or cyclopentamethyleneimino group and the substituents for the substituted cycloalkyl, phenyl, benzyl, phenethyl and heterocyclic radicals specified hereinabove being selected from the group consisting of bromine, chlorine, cyano, alkyl having 1 to 3 carbon atoms and alkoxy having 1 to 2 carbon atoms. The above-mentioned heteroaryl residues having 4 to 7 carbon atoms may be pyridyl, thiazolyl, benzthiazolyl, imidazolyl, benzimidazolyl, thienyl, furyl or pyrrolyl groups.

The starting materials for the preparation of the novel compounds of formula I are 2,6-dihydroxypyridine derivatives of the formula: ##SPC3##

wherein X and Y having the above-stated meaning. These starting compounds may be prepared in a known manner analogous to the method described by Bobbitt and Scola, Journ. of Org. Chem. 25, 560: by the condensation of correspondingly substituted acetic acid amides with correspondingly substituted β-ketocarboxylic acid esters. They may also be prepared in accordance with various other processes, as described for example in the monograph "Heterocyclic Compounds Pyridine and its Derivatives Part. 3" by Klingsberg. This monograph has appeared in the frame of the series published by Arnold Weissberger "The Chemistry of Heterocyclic Components", Interscience Publishers. The 2,6-dihydroxypyridine derivatives of formula II, according to Bobbitt and Scola, ibid., are converted by means of phosphoroxychloride or analogously by means of phosphoroxybromide at 180°C. into the corresponding 2,6-dichloro or 2,6-dibromopyridine derivatives of formula III: ##SPC4##

wherein X and Y have the above-stated meanings and Hal is bromine or preferably chlorine.

For the preparation of compounds of formula I, wherein Z₂ stands for chlorine or bromine and to which formula Ia then pertains, a compound of formula III is reacted with a compound of formula IV in accordance with the reaction: ##SPC5##

Q in this instance is hydrogen or a metal, preferably an alkali metal such as sodium or potassium. In the event that Z₁ stands for --So₂ R₁₂, zinc is especially preferred.

Reaction (1) is carried out in equimolar ratio at temperatures of 20°-100°C. in a suitable inert solvent. The exchange of the chlorine or bromine atom in the 6-position is ascertained by analysis of the NMR absorption of the obtained compounds of formula Ia.

To the extent that in formula IV, Z₁ stands for the radicals: ##EQU8## hydrogen is appropriately selected for Q, i.e., in the reaction equation (1) formula IV then stands for the compounds ##EQU9## In this instance, the reaction is carried out in accordance with reaction equation (1), preferably in the temperature range of 20° to 50°C. and as suitable inert solvents, alkanols with a chain length of 1 to 4 carbon atoms are preferably used. In those instances where the physical properties are appropriate, an excess of one of the reaction constituents may also serve as the solvent.

To the extent that in formula IV, Z₁ stands for cyano or for --SO₂ R₁₂, a metal is appropriately selected for Q, preferably an alkali metal such as sodium or potassium and in the event that Z₁ is SO₂ R₁₂, zinc is particularly preferred. In reaction equation (1), formula IV then stands for the compounds NaCN, KCN and Zn(SO₂ R₁₂)₂. In this instance, the reaction in accordance with reaction equation (1) is carried out preferably in the temperature range of 60°-80°C. in a suitable organic solvent such as an alcohol, ether, ester, carboxylic acid amide, N-substituted carboxylic acid amide such as dimethylformamide, dialkylsulfoxide such as dimethylsulfoxide or dialkylsulfone, all of these preferably having not more than 6 carbon atoms. In the reaction of sulfinates, the addition of a copper-I-salt is advantageous.

To the extent that in formula IV, Z₁ stands for the radicals --OR₁₂ or --SR₁₂, a metal atom is selected for Q, preferably an alkali metal atom such as sodium or potassium. In reaction equation (1), formula IV then stands for the compounds NaOR₁₂, NaSR₁₂, KOR₁₂ and KSR₁₂. In this instance, the reaction is conducted in accordance with reaction equation (1), preferably in the temperature range of 60°-100°C., in an inert organic solvent, e.g., an aromatic hydrocarbon such as benzene, toluene or xylene, or in an excess of the reaction constituent HOR₁₂ or HSR₁₂ as the solvent.

The compounds of formula Ia may be further reacted in accordance with the reaction: ##SPC6##

This reaction is carried out at temperatures of 20°-200°C. in a suitable solvent. The molar ratio of reactants is 1:1.

When Z₂ is OH in the compound of formula V, there is used a suitable alkali metal hydroxide such as sodium hydroxide or potassium hydroxide in an aqueous or aqueous-alcoholic medium. However, sodium carbonate, potassium hydroxide or similar compounds which release hydroxyl ions in an aqueous medium may also be used. The solvents may be alkanols having 1 to 4 carbon atoms. The preferred temperature range is 70°-150°C.

If Z₂ is --SH in the compound of formula V, an alkali metal hydrosulfide, preferably NaSH or KSH, is used and the reaction is carried out in an aqueous medium, preferably at temperatures of 100°-150°C.

In the event Z₂ stands for --OR₁₂ or --SR₁₂, an alkali metal, preferably sodium or potassium, is selected for Q in formula V and the reaction constituents are reacted at temperatures of 60°-150°C., preferably at 60°-100°C., in a suitable inert solvent, e.g., an aromatic hydrocarbon such as benzene, toluene or xylene, or in an excess of the reaction constituent HOR₁₂ or HSR₁₂ as solvent.

In the event Z₂ is cyano or --SO₂ R₁₂ in formula V, a metal is selected for Q, preferably an alkali metal such as sodium or potassium or when Z₂ is --SO₂ R₁₂, zinc is also useful. The reaction between these compounds of formulae Ia and V is carried out in a suitable organic solvent at temperatures of 20°-100°C. and preferably 60°-80°C. Suitable organic solvents, for example, include alcohols, ethers, esters, carboxylic acid amides, N-substituted carboxylic acid amides such as dimethylformamide, dialkylsulfoxides such as dimethylsulfoxide or dialkylsulfones, all having preferably not more than 6 carbon atoms. In the use of sulfinates, the addition of a copper-I-salt is advantageous.

In the event Z₂ is ##EQU10## in formula V, hydrogen is selected for Q, and the constituents are reacted at 100°-200°C., preferably at 160°-180°C., in an inert solvent, preferably an alkanol having 1 to 4 carbon atoms or, in those instances where the physical properties are appropriate, an excess of one of the reaction constituents may be used as the solvent.

Novel compounds wherein Z₂ has the same meaning as Z₁ may be prepared in accordance with the reaction: ##SPC7##

wherein a compound of formula III is reacted with a compound of formula IV in a molar ratio of at least 1:2 in a suitable solvent at temperatures of 20° to 200°C. When Z₁ is ##EQU11## in formula IV, hydrogen is selected for Q, and when Z₁ is --CN, --OR₁₂, --SR₁₂ or --SO₂ R₁₂, a metal is selected for Q, preferably an alkali metal such as sodium or potassium. Also when Z₁ is --SO₂ R₁₂, zinc is suitable. Suitable solvents are alcohols, ethers, hydrocarbons etc. The selection of the solvent may be the same as described for reaction (1).

Novel compounds when Z₂ is --OH may also be prepared by the reaction of a 2 -hydroxy-6-bromo- or 2-hydroxy-6-chloropyridine derivative of formula VI with a compound of formula IV in a molar ratio of 1:1 in accordance with reaction: ##SPC8##

The reaction is carried out in a suitable solvent at temperatures of 20° to 100°C. The data respecting the solvents and the meaning and selection of Q set forth above for reaction equations (1) and (3), apply to reaction (4).

Compounds of formula VI may be prepared by the reaction of the corresponding 2,6-dihydroxypyridine compounds with phosphoroxychloride or phosphoroxybromide at 80°-100°C. in an inert organic solvent such as benzene, toluene or xylene.

If reactions (1) through (4) are carried out at temperatures which are above the boiling point of a reaction constituent or of the solvent used, then the utilization of excess pressure is required.

Compounds of formulae Ia, Ib and Ic are preferred groups of novel compounds. Further preferred compounds are those wherein in formula I:

X is alkyl having 1 to 3 carbon atoms, preferably methyl,

Y is cyano,

Z₁ is cyano, alkoxy having 1 to 2 carbon atoms, alkylsulfonyl having 1 to 2 carbon atoms, amino, monoalkylamino having 1 to 3 carbon atoms or monoalkylamino having 1 to 3 carbon atoms and substituted by alkoxy having 1 to 2 carbon atoms and

Z₂ is cyano, hydroxyl, alkoxy having 1 to 2 carbon atoms, alkylsulfonyl having 1 to 2 carbon atoms, amino, monoalkylamino having 1 to 3 carbon atoms or monoalkylamino having 1 to 3 carbon atoms and substituted by alkoxy having 1 to 2 carbon atoms.

Such preferred compounds are especially the pyridine compounds of the formulae: ##SPC9##

It is possible that the novel compounds of formula I in part exist in tautomeric forms. For example, the following tautomeric formulae are possible. ##SPC10##

As used herein, formula I is also understood to embrace such possible tautomers.

As the reaction constituents of formula III such as 2,6-dichloro or 2,6-dibromo pyridine derivatives are suitable, for example, which in the X position contain hydrogen or a methyl, ethyl, n-propyl, isopropyl, vinyl, α-methylvinyl, n-butyl, isobutyl, sec.-butyl, n-amyl or isoamyl, n-hexyl, 2-dimethylaminoethyl, 2-diethylaminoethyl, 2-morpholinoethyl, 2-piperidinoethyl, 2-pyrrolidinoethyl, N-methyl-N'-piperazinoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-acetoxyethyl, 2-phenoxyacetoxyethyl, N-ethylcarbamoyloxyethyl, N-phenylcarbamoyloxyethyl, 2-phenoxyethyl, 3-methoxypropyl, cyclohexyl, benzyl, 3-methylbenzyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-chlorophenyl, 4-chlorophenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2,5-dimethyl-4-chlorophenyl or the following radicals: ##SPC11##

The compounds of formula III may, in the Y position, contain for example hydrogen, cyano, amino, nitroso, nitro, methyl, ethyl, 2-hydroxyethyl, 2-cyanoethyl, 2-acetoxyethyl, 2-benzoyloxyethyl, 2-methoxyethyl, 2-phenoxyethyl, 2-monoethylaminoethyl, 2-monomethylaminoethyl, 2-dimethylaminoethyl, 2-diethylaminoethyl, 2-morpholinoethyl, 2-piperidinoethyl, 2-pyrrolidinoethyl, n-propyl, isopropyl, vinyl, α-methylvinyl, n-butyl, isobutyl, sec.-butyl, n-amyl, isoamyl, n-hexyl, cyclohexyl, benzyl, phenyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec.-butyloxycarbonyl, n-amyloxycarbonyl, n-isoamyloxycarbonyl, n-hexyloxycarbonyl, acetyl, acryloyl, propionyl, capronyl, capryl, hexahydrobenzoyl, phenacetyl, benzoyl, 4-methylbenzoyl, 2,4-dimethylbenzoyl, 4-methoxybenzoyl, 4-chlorbenzoyl, aminocarbonyl, monomethylaminocarbonyl, dimethylaminocarbonyl, ethyleniminocarbonyl, monoethylaminocarbonyl, monoisopropylaminocarbonyl, diethylaminocarbonyl, monooxethylaminocarbonyl, mono-γ-methoxypropylaminocarbonyl, morpholinocarbonyl, piperidinocarbonyl, cyclohexylaminocarbonyl, benzylaminocarbonyl, anilinocarbonyl, 4-methylanilinocarbonyl, N-methylanilinocarbonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec.-butylsulfonyl, n-amylsulfonyl, isoamylsulfonyl, n-hexylsulfonyl, benzylsulfonyl, phenylsulfonyl, 4-methylphenylsulfonyl, 2,4-dimethylphenylsulfonyl, 4-methoxyphenylsulfonyl, 4-chlorphenylsulfonyl, aminosulfonyl, monomethylaminosulfonyl, dimethylaminosulfonyl, ethyleniminosulfonyl, monoethylaminosulfonyl, monoisopropylaminosulfonyl, diethylaminosulfonyl, monooxethylaminosulfonyl, mono-γ-methoxypropylaminosulfonyl, morpholinosulfonyl, piperidinosulfonyl, cyclohexylaminosulfonyl, benzylaminosulfonyl, anilinosulfonyl, 4-methylanilinosulfonyl, N-methylanilinosulfonyl or the radicals ##SPC12##

Of course, suitable starting compounds of formula III are also such 2,6-dichloro or 2,6-dibromopyridine derivatives which are identically substituted in the X and Y position, the preferred substituents being those which were indicated above for the X position.

Suitable reaction constituents ##EQU12## of formulae IV and V include, for example, the following primary and secondary amines and diamines:

Primary Amines

ammonia, methylamine, ethylamine, 2-hydroxyethylamine, 2-methoxyethylamine, 3-phenoxyethylamine, 3-cyanoethylamine, n-propylamine, isopropylamine, 3-hydroxypropylamine-(1), 3-methoxypropylamine-(1), 3-isopropoxypropylamine-(1), 3-cyanopropylamine-(1), allylamine, 1-methallylamine, 2-methallylamine, n-butylamine, isobutylamine, sec.-butylamine, tert.-butylamine, 2-amino-2-methylpropanol-(1), crotylamine, 3-aminopentane, n-amylamine, isoamylamine, n-hexylamine, cyclohexylamine, benzylamine, 2-phenylethylamine, aniline, 4-methylaniline, 4-methoxyaniline, 2,4-dimethylaniline, 1-aminonaphthaline, 2-aminonaphthaline, ##SPC13##

Secondary Amines

dimethylamine, diethylamine, N-(2-cyanoethyl)-N-(2-hydroxyethyl)-amine, N-di-(2-hydroxyethyl)-amine, N-di-(2-cyanoethyl)-amine, N-methyl-(2-hydroxyethyl)-amine, N-isopropyl-(2 -hydroxyethyl)-amine, N-n-butyl-(2-hydroxyethyl)-amine, N-cyclohexyl-(2-hydroxyethyl)-amine, N-benzyl-(2-hydroxyethyl)-amine, di-n-propylamine, di-isopropylamine, di-n-butylamine, di-isobutylamine, di-n-amylamine, di-n-hexylamine, morpholine, pyrrolidine, piperidine, N-methylpiperazine, N-methylcyclohexylamine, N-ethylcyclohexylamine, N-methylbenzylamine, N-methyl-3-methylbenzylamine, N-methylaniline, N-ethylaniline, N-2-hydroxyethylaniline, N-benzylaniline, N-methyl-2-chloraniline and N-ethyl-2-chloraniline.

Diamines

N-methyl-N',N'-dimethylhydrazine, N,N-dimethylhydrazine, N,N-diethylhydrazine, N-methyl-N-phenylhydrazine, N-aminopyrrolidine, N-aminopiperidine, N-aminopiperazine, N-aminomorpholine, N,N-dimethylethylenediamine, N,N-diethylethylenediamine, N,N-dimethylpropylenediamine-(1,3), or N,N-diethylpropylenediamine-(1,3), 2-morpholinoethylamine, 2-piperidinoethylamine, 2-pyrrolidinoethylamine and N-methyl-N'-3-amino-n-propylpiperazine of the formula: ##EQU13##

Suitable reaction constituents H₂ NOR₁₀ or ##EQU14## according to the general formulae IV and V, for example, are:

Hydroxylamines ##EQU15##

As the hetarylamines for Z₁ and Z₂, the following may, for example, be used:

3-aminodiphenylene oxide

3-aminodiphenylene sulfide

3-aminodiphenylene sulfone

2-aminocarbazole

3-amino-N-methylcarbazole

3-amino-N-ethylcarbazole

3-amino-N-β-hydroxyethylcarbazole

3-amino-N-β-cyanoethylcarbazole

3-amino-N-n-propylcarbazole

3-amino-N-isopropylcarbazole

3-amino-N-(β-dimethylaminoethyl)-carbazole

3-amino-N-(β-diethylaminoethyl)-carbazole

3-amino-N-(γ-dimethylaminopropyl)-carbazole

3-amino-N-(α-methyl-β-dimethylaminoethyl)-carbazole

As the compounds HO-R₁₂ or HS-R₁₂, which after their conversion into the corresponding metal compounds, particularly the corresponding alkali metal compounds (especially the corresponding sodium and potassium compounds) are suitable as reaction constituents of formulae IV and V, the following alcohols, phenols or the corresponding mercaptans and thiophenols may be utilized: methanol, ethanol, 2-cyano-methanol-(1), ethylene glycol monomethyl ether, ethylene glycol monoethylether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butylether, ethylene glycol monophenyl ether, ethylene glycol monoxylenyl ether, diethylene glycol monomethylether, diethylene glycol monoethylether, diethylene glycol mono-n-butylether, triethylene glycol monomethylether, triethylene glycol monoethylether, triethylene glycol mono-n-butylether, n-propanol, isopropanol, propene-(1)-ol-(3), 2-methylpropene-(1)-ol-(3), n-butanol, sec.-butanol, isobutanol, tert.-butanol, 3-methoxybutanol-(1), 4-methoxybutanol-(1), butene-(1)-ol-(2), n-pentanol, isopentanol, n-hexanol, cyclohexanol, 4-methylcyclohexanol, 4-methoxycyclohexanol, phenylmethanol, (4-chlorophenyl)-methanol, phenylethanol, (4-cyanophenyl)-ethanol, phenol, 2-methylphenol, 3-methylphenol, 4-methylphenol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 2-methoxy-3-methylphenol, 2-methoxy-4-methylphenol, 2-methoxy-5-methylphenol, 2-methoxy-6-methylphenol, 3-methoxy-5-methylphenol, 3-methoxy-6-methylphenol, 4-methoxy-5-methylphenol, 4-methoxy-6-methylphenol, 2,3-dimethoxyphenol, 2,4 -dimethoxyphenol, 3,5-dimethoxyphenol, 2-chlorophenol, 3-chlorophenol, 4-chlorophenol, 2-bromophenol, 3-bromophenol, 4-bromophenol, 2-cyanophenol, 3-cyanophenol, 4-cyanophenol, 2,3-dichlorophenol, 2,4-dichlorophenol, 2,5-dichlorophenol, 2,6-dichlorophenol, 3,4-dichlorophenol, 3,5-dichlorophenol, 2,3-dibromophenol, 2,4-dibromophenol, 2,5-dibromophenol, 2,6-dibromophenol, 3,4-dibromophenol, 3,5-dibromophenol, 2-methyl-3-chlorophenol, 2-methyl-4-chlorophenol, 2-methyl-5-chlorophenol, 2-methyl-6-chlorophenol, 2-methyl-3-bromophenol, 2-methyl-4-bromophenol, 2-methyl-5-bromophenol, 2-methyl-6-bromophenol, 3-methyl-2-chlorophenol, 3-methyl-4-chlorophenol, 3-methyl-6-chlorophenol, 3-methyl-2-bromophenol, 3-methyl-4-bromophenol, 3-methyl-6-bromophenol, 4-methyl-5-chlorophenol, 4-methyl-6-chlorophenol, 4-methyl-5-bromophenol, 4-methyl-6-bromophenol, 4-chloropyrocatechol-1-methylether, 5-chloropyrocatechol-1-methylether, 4-bromopyrocatechol-1-methylether, 5-bromopyrocatechol-1-methylether, 4-chloroesorcinol-1-methylether, 4-chlororesorcinol-3-methylether, 4-bromoresorcinol-1-methylether, 4-bromoresorcinol-3-methylether, 2-chlorohydroquinone-1-methylether, 2-chlorohydroquinone-2-methylether, 5-chlororesorcinol-1-methylether, 1-naphthol, 2-naphthol, 2-methyl-1-naphthol, 3-methyl-1-naphthol, 4-methyl-1-naphthol, 7-methyl-1-naphthol, 3,6-dimethyl-1-naphthol, 3,7-dimethyl-1-naphthol, 4,6-dimethyl-1-naphthol, 4,7-dimethyl-1-naphthol, 6,7-dimethyl-1-naphthol, 4-methoxy-1-naphthol, 5-methoxy- 1-naphthol, 6-methoxy-1-naphthol, 7-methoxy-1-naphthol, 8-methoxy-1-naphthol, 2-chloro-1-naphthol, 3-chloro-1-naphthol, 4-chloro-1-naphthol, 5-chloro-1-naphthol, 7-chloro-1-naphthol, 8-chloro-1-naphthol, 2,3-dichloro-1-naphthol, 2,4-dichloro-1-naphthol, 5,7-dichloro-1-naphthol, 5,8-dichloro-1-naphthol, 2-chloro-4-bromo-1-naphthol, 2-bromo-1-naphthol, 3-bromo-1-naphthol, 4-bromo-1-naphthol, 5-bromo-1-naphthol, 6-bromo-1-naphthol, 7-bromo-1-naphthol, 8-bromo-1-naphthol, 2-ethyl-4-bromo-1-naphthol, 2,4-dibromo-1-naphthol, 1-methyl-2-naphthol, 6-methyl-2-naphthol, 1,4-dimethyl-2-naphthol, 3,6-dimethyl-2-naphthol, 3,7-dimethyl-2-naphthol, 6,7-dimethyl-2-naphthol, 1-chloro-2-naphthol, 3-chloro-2-naphthol, 4-chloro-2-naphthol, 5-chloro-2-naphthol, 6-chloro-2-naphthol, 7-chloro-2-naphthol, 8-chloro-2-naphthol, 1,3-dichloro-2-naphthol, 1,4-dichloro-2-naphthol, 1-bromo-2-naphthol, 3-bromo-2-naphthol, 4-bromo-2-naphthol, 5-bromo-2-naphthol, 6-bromo-2-naphthol, 7-bromo-2-naphthol, 8-bromo-2-naphthol, 1-methyl-6-bromo-2-naphthol, 1-ethyl-6-bromo-2-naphthol, 1,6-dibromo-2-naphthol, 3,6-dibromo-2-naphthol, 3,7-dibromo-2-naphthol and 4,6-dibromo-2-naphthol.

For the preparation of the novel compounds of formula I, wherein the substituent Z₁ and/or Z₂ signifies a --SO₂ --R₁₂ radical, sulfinates are employed, preferably zinc sulfinates of the formula Zn (SO₂ --R₁₂)₂. They allow the introduction of, for example, the following radicals: methylsulfonyl, chloromethylsulfonyl, ethylsulfonyl, 2-chloroethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec.-butylsulfonyl, n-amylsulfonyl, isoamylsulfonyl, n-hexyl-sulfonyl, cyclohexylsulfonyl, benzylsulfonyl, phenylsulfonyl, 2,4-dimethylphenylsulfonyl, 4-methylphenylsulfonyl, 4-methoxyphenylsulfonyl, 4-chlorophenylsulfonyl, 4-chloro-3-methylphenylsulfonyl and 4-bromophenylsulfonyl.

The compounds of the present invention are valuable intermediates, in particular for the preparation of dyestuffs, preferably of azo dyestuffs. As far as these azo dyes do not contain ionogenic groups, they may be employed as disperse dyes for dyeing and printing synthetic hydrophobic fiber material, whereas those azo dyes which do contain ionogenic groups are suited for dyeing and printing cotton, wool, silk, polyamide and modified polyacrylonitrile.

Moreover, the compounds of the present invention are valuable pest control agents -- in particular if they are employed as insectizides -- , as well as valuable pharmaceuticals -- above all if they are employed as analeptics, analgetics and diuretics.

Azo dyes containing the compounds of the present invention may be prepared, for instance, by diazotizing a diazotizable aromatic amine and coupling it with a compound of the present invention. The diazotization and the coupling are carried out in the usual manner. According to the respective initial products employed, this working method leads to the preparation, for instance, of disperse dyes, reactive dyes, cationic dyes or acid dyes. All of these azo dyes exhibit outstanding tinctorial properties, in particular a high coloring strength and a very good fastness to light, perspiration, water, sea water, alkalies and to washing. The disperse dyes distinguish themselves above all by an excellent fastness to dry-heat pleating and setting, ozone, waste-gas fading and to rubbing, by a high resistance when subjected to various permanent press treatments and by a good covering power even when applied onto textured polyester materials. The reactive dyes distinguish themselves in particular by an even color depth obtained in the different setting processes. The azo dyes mentioned hereinbefore are suited for dyeing and printing textile materials according to various known processes. The preparation of the dyes as well as their application for dyeing and printing are described in Examples 15 - 19.

In the following examples, "p.b.w." means parts by weight.

EXAMPLE 1

To a composition of 320 p.b.w. ethyl alcohol and 83.7 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine, which are placed in an autoclave, there are added 51.0 p.b.w. liquid ammonia and subsequently the reaction liquid is heated for 18 hours at 200°C. After cooling, the ethyl alcohol is then distilled off, the residue agitated with 300 p.b.w. water, drawn off, washed with water and dried. The resulting 2,6-diamino-3-cyano-4 -methylpyridine having the formula ##SPC14##

may be purified by crystallization from ethyl alcohol.

Analysis: C₇ H₈ N₄ Calculated: 37.8% N Found: 37.4% N.

EXAMPLE 2

A solution of 400 p.b.w. ethyl alcohol, 93.0 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine and 274.0 p.b.w. diethylamine is agitated 24 hours at 50°C. Upon cooling of the reaction solution, the resulting 2-chloro-3-cyano-4-methyl-6-diethylaminopyridine of the formula ##SPC15##

EXAMPLE 4

Introduced into 200 p.b.w. methyl alcohol while cooling were 3.7 p.b.w. sodium. Added to this sodium methyl solution then were 33.5 p.b.w. 2-chloro-3-cyano-4-methyl-6-diethylaminopyridine and subsequently the reaction solution was heated to the point of boiling for 24 hours. Then the methyl alcohol was distilled off, the residue taken up with 100 p.b.w. water, drawn off, washed with water and dried. The resulting 2-methoxy-3-cyano-4-methyl-6-diethylaminopyridine of the formula ##SPC16##

may be purified by recrystallization from methanol.

Analysis: C₁₂ H₁₇ N₃ O Calculated: 19.2 % N 14.2 % --OCH.sub. 3 . Found: 19.0 % N 13.8 % --OCH₃ .

EXAMPLE 5

A composition consisting of 432 p.b.w. n-propylamine and 187 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine is agitated in an autoclave for 2 hours at 100°C. Upon cooling, the reaction liquor is decomposed in water, the resulting 2-chloro-3-cyano-4-methyl-6-n-propylaminopyridine having the formula ##SPC17##

is crystallized out. The pyridine derivative is then drawn off and washed on the suction apparatus first with 100 p.b.w. ethyl alcohol and subsequently with 500 p.b.w. water. The substance is analytically pure. Its constitution, i.e., the exchange of the 6-position halogen atom in the 2,6-dichloro-3-cyano-4-methylpyridine against the diethylamino group was assured by MNR absorption analysis.

Analysis: C₁₁ H₁₄ ClN₃ Calculated: 18.8% N 15.7% Cl. Found: 18.5% 15.7% Cl.

EXAMPLE 3

The mixture of Example 2 is agitated in an autoclave for 12 hours at 150°C. Upon cooling, the ethyl alcohol is then distilled off and the residue agitated with 50 p.b.w. water and 245 p.b.w. soda lye, 33° Be. The resulting 2,6-bis-(diethylamino)-3-cyano-4-methylpyridine of the formula ##SPC18##

is an oil which is isolated with ether. It may be purified by vacuum distillation.

Analysis: C₁₅ H₂₄ N₄ Calculated: 21.5% N. Found: 21.5% N. is drawn off and washed with water. It may be purified by recrystallization from ethyl alcohol.

Analysis: C₁₀ H₁₂ ClN₃ Calculated: 20.1% N 16.7% Cl. Found: 20.3% N 17.0% Cl.

EXAMPLE 6

A composition of 100 p.b.w. 3-dimethylaminopropylamine(1) and 41.8 p.b.w. 2-chloro-3-cyano-4-methyl-6-n-propylaminopyridine are agitated for 2 hours at 140°C. The reaction melt upon cooling is stirred with water, the residue is drawn off and washed with water. The resulting 2-(3'-dimethylamino-n-propylamino)-3-cyano-4-methyl-6-n-propylaminopyridine having the formula ##SPC19##

may be purified by crystallization from ethyl alcohol.

Analysis: C₁₅ H₂₅ N₅ Calculated: 25.4% N. Found: 25.2% N.

EXAMPLE 7

Introduced into a solution of 155 p.b.w. monomethylamine in 1000 p.b.w. isopropylalcohol are 187 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine. Subsequently, the reaction solution is heated in an autoclave for 5 hours at 200°C. Upon cooling to room temperature, the resulting 2,6-bis-(monomethylamino)-3-cyano-4-methylpyridine having the formula ##SPC20## is drawn off, first washed with isopropyl alcohol, then with water and dried. It may be purified by crystallization from isopropyl alcohol.

Analysis: C₉ H₁₂ N₄ Calculated: 31.8% N. Found: 32.0% N.

EXAMPLE 8

A composition of 200 p.b.w. ethyl alcohol, 83.7 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine and 180 p.b.w. 3-methoxypropylamine-(1) is heated in an autoclave for 18 hours at 180°C. Upon cooling, the ethyl alcohol is distilled off, the residue is stirred with 100 p.b.w. water with the addition of 150 p.b.w. soda lye, 33°Be, drawn off, washed with water and dried. The resulting 2,6-bis-(3'-methoxy-n-propylamino)-3-cyano-4-methylpyridine having the formula ##SPC21##

may be purified by vacuum distillation.

Analysis: C₁₅ H₂₄ N₄ O₂ Calculated: 19.2% N. Found: 19.6% N.

EXAMPLE 9

A composition consisting of 100 p.b.w. morpholine and 37.4 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine is heated for 30 minutes at 130°C. The reaction melt is then decomposed on ice, the residue is drawn off, washed with water, and dried. The resulting 2,6-bis-(morpholino)-3-cyano-4-methylpyridine having the formula ##SPC22##

may be purified by crystallization from ethyl alcohol.

Analysis: C₁₅ H₂₀ N₄ O₂ Calculated: 19.4% N. Found: 19.7% N.

EXAMPLE 10

There are introduced 37.2 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine into 150.0 p.b.w. aniline. This reaction solution is then heated for 24 hours at 150°C. and subsequently decomposed in 1000 p.b.w ice with the addition of 350 p.b.w. crude hydrochloric acid (D = 1.153). The resulting 2,6-bis-(anilino)-3-cyano-4-methylpyridine having the formula ##SPC23##

may be purified by crystallization from ethyl alcohol.

Analysis: C₁₉ H₁₆ N₄ Calculated: 18.7% N. Found: 18.5% N.

EXAMPLE 11

Introduced into 80 p.b.w. methyl alcohol are 7.6 p.b.w. sodium during cooling, then there are added 27.9 p.b.w. 2,6-dichloro-3-cyano-4-methylpyridine to this sodium methylate solution and subsequently the reaction solution is heated to the point of boiling for 24 hours. Then the methyl alcohol is distilled off. The residue is taken up with 100 p.b.w. water, drawn off, washed with water and dried. The resulting 2,6-dimethoxy-3-cyano-4-methylpyridine having the formula ##SPC24##

may be purified by recrystallization from methyl alcohol.

Analysis: C₉ H₁₀ N₂ 0₂. Calculated: 15.7% N 34.8% --OCH₃. Found: 15.5% N 34.2% --OCH₃.

EXAMPLE 12

There are introduced 27.9 p.b.w. of 2,6-dichloro-3-cyano-4-methylpyridine into a sodium ethylate solution, which had been prepared from 80 p.b.w. ethyl alcohol and 3.8 p.b.w. sodium. Subsequently, the reaction solution is heated to the point of boiling for 24 hours. The ethyl alcohol is then distilled off, the residue is stirred with 100 p.b.w. water, and the resulting 2-chloro-3-cyano-4-methyl-4-ethoxypyridine having the formula ##SPC25##

is taken up with ether. It may be purified by vacuum distillation.

Analysis: C₉ H₉ ClN₂ O. Calculated: 14.3% N 17.8% Cl. Found: 14.5% N 17.6% Cl.

In the following table there are presented further pyridine compounds prepared in accordance with the herein described process: ##SPC26##

or tautomeric formulae.

                                                   Empirical                                                                              Cal'd.                                                                             Found               No.                                                                               Z.sub.1               Z.sub.2               Formula N%  N%                  __________________________________________________________________________     1. --NHCH.sub.2 CH.sub.3 --NHCH.sub.2 CH.sub.3 C.sub.11 H.sub.16 N.sub.4                                                              27.5                                                                               27.5                2. --NHCH.sub.2 CH.sub.2 OH                                                                             --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.11 H.sub.16 N.sub.4                                                      O.sub.2 23.7                                                                               24.0                3. --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                      --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                      C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2 21.2                                                                               21.0                4. --NHCH.sub.2 CH.sub.2 CN                                                                             --NHCH.sub.2 CH.sub.2 CN                                                                             C.sub.13 H.sub.14 N.sub.6                                                              33.1                                                                               33.5                5. --NHCH.sub.2 CH.sub.2 CH.sub.3                                                                       --NHCH.sub.2 CH.sub.2 CH.sub.3                                                                       C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               24.6                   CH.sub.3              CH.sub.3                                              6. --NH--CH∠       --NH--CH∠       C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               24.4                   CH.sub.3              CH.sub.3                                              7. --NH--(CH.sub.2).sub.2 CH.sub.2 OCH.sub.3                                                            --NH--(CH.sub.2).sub.2 CH.sub.2 OCH.sub.3                                                            C.sub.15 H.sub.24 N.sub.4                                                      O.sub.2 19.2                                                                               19.0                8. --NHCH.sub.2 CH=CH.sub.2                                                                             --NHCH.sub.2 CH=CH.sub.2                                                                             C.sub.13 H.sub.16 N.sub.4                                                              24.6                                                                               24.2                9. --NH--C.sub.4 H.sub.9 (n)                                                                            --NH--C.sub.4 H.sub.9 (n)                                                                            C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               21.8                10.                                                                               --NH--C.sub.4 H.sub.9 (sec)                                                                          --NH--C.sub.4 H.sub.9 (sec)                                                                          C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               21.3                   CH.sub.2 --CH.sub.3   CH.sub.2 --CH.sub.3                                      --NH--CH∠       --NH--CH∠       C.sub.17 H.sub.28 N.sub.4                                                              19.4                                                                               19.8                   CH.sub.2 --CH.sub.3   CH.sub.2 --CH.sub.3                                      --NH--C.sub.5 H.sub.11 (iso)                                                                         --NH--C.sub.5 H.sub.11 (iso)                                                                         C.sub.17 H.sub.28 N.sub.4                                                              19.4                                                                               19.6                   --NH--C.sub.6 H.sub.13 (n)                                                                           --NH--C.sub.6 H.sub.13 (n)                                                                           C.sub.19 H.sub.34 N.sub.4                                                              17.7                                                                               18.1                14.                                            C.sub.19 H.sub.28 N.sub.4                                                              17.9                                                                               17.5                15.                                            C.sub.21 H.sub.20 N.sub.4                                                              17.1                                                                               17.5                16.                                            C.sub.23 H.sub.24                                                                      15.7b.4                                                                            15.5                17.                                            C.sub.27 H.sub.20 N.sub.4                                                              14.0                                                                               14.3                   HC------CN            HC------CH            C.sub.17 H.sub.16 N.sub.4                                                      O.sub.2 18.2                                                                               18.5                   ∥∥  ∥∥                                     HCC--CH.sub.2 --NH--  HCC--CH.sub.2 --NH--                                     ∠               ∠                                                  O                     O                                                     19.                                            C.sub.19 H.sub.18 N.sub.6                                                              25.5                                                                               25.7                20.                                                                               H.sub.2 C------CH--NH--                                                                              H.sub.2 C------CH--NH--                                                                              C.sub.15 H.sub.20 N.sub.4                                                      O.sub.4 S.sub.2                                                                        14.6                                                                               15.0                   ||  ||                                     H.sub.2 CCH.sub.2     H.sub.2 C CH.sub.2                                       ∠               ∠                                                  S                     S                                                        O.sub.2               O.sub.2                                               21.                                            C.sub.25 H.sub.22 N.sub.6                                                              20.7                                                                               21.0                   CH.sub.3              CH.sub.3                                                 --N∠            --N∠            C.sub.11 H.sub. 16                                                                     27.5b.4                                                                            27.2                   CH.sub.3              CH.sub.3                                                 CH.sub.2 CH.sub.2 CN  CH.sub.2 CH.sub.2 CN                                     --N∠            --N∠            C.sub.19 H.sub.20 N.sub.8                                                              31.1                                                                               36.7                   CH.sub.2 CH.sub.2 CN  CH.sub.2 CH.sub.2 CN                                     CH.sub.2 CH.sub.2 CN  CH.sub.2 CH.sub.2 CN                                     --N∠            --N∠            C.sub.17 H.sub.22 N.sub.6                                                      O.sub.2 26.3                                                                               26.8                   CH.sub.2 CH.sub.2 OH  CH.sub.2 CH.sub.2 OH                                     CH.sub.3              CH.sub.3                                                 --N∠            --N∠            C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2 21.2                                                                               21.6                   CH.sub.2 CH.sub.2 OH  CH.sub.2 CH.sub.2 OH                                     C.sub.4 H.sub.9 (n)   C.sub.4 H.sub.9 (n)                                      --N∠            --N∠            C.sub.19 H.sub.32 N.sub.4                                                      O.sub.2 16.1                                                                               16.5                   CH.sub.2 CH.sub.2 OH  CH.sub.2 CH.sub.2 OH                                  27.                                            C.sub.23 H.sub.36 N.sub.4                                                      O.sub.2 14.0                                                                               14.6                28.                                            C.sub.25 H.sub.28 N.sub.4                                                      O.sub.2 13.5                                                                               13.2                   C.sub.3 H.sub.7 (n)   C.sub.3 H.sub.7 (n)                                      --N∠            --N∠            C.sub.19 H.sub.32 N.sub.4                                                              17.7                                                                               18.2                   C.sub.3 H.sub.7 (n)   C.sub.3 H.sub.7 (n)                                      C.sub.4 H.sub.9 (n)   C.sub.4 H.sub.9 (n)                                   30.                                                                               --N∠            --N∠            C.sub.23 H.sub.40 N.sub.4                                                              15.1                                                                               15.5                   C.sub.4 H.sub.9 (n)   C.sub.4 H.sub.9 (n)                                      C.sub.6 H.sub.13 (n)  C.sub.6 H.sub.13 (n)                                     --N∠            --N∠            C.sub.31 H.sub.56 N.sub.4                                                              11.6                                                                               11.2                   C.sub.6 H.sub.13 (n)  C.sub.6 H.sub.13 (n)                                     --NHO                 --NHO                 C.sub.15 H.sub.20 N.sub.4                                                      O.sub.2 19.4                                                                               19.6                33.                                            C.sub.17 H.sub.24 N.sub.4                                                              19.7                                                                               19.3                   --NHN--CH.sub.3       --NHN--CH.sub.3       C.sub.17 H.sub.26 N.sub.6                                                              26.8                                                                               26.2                   --NHN--C.sub.2 H.sub.5                                                                               --NHN--C.sub.2 H.sub.5                                                                               C.sub.19 H.sub.20 N.sub.6                                                              24.6                                                                               25.1                36.                                            C.sub.15 H.sub.20 N.sub.4                                                              21.8                                                                               22.2                37.                                            C.sub.21 H.sub.22 N.sub.6                                                              23.5                                                                               23.8                   CH.sub.3              CH.sub.3                                                 --NH--N∠        --NH--N∠        C.sub.11 H.sub.18 N.sub.6                                                              35.9                                                                               35.6                   CH.sub.3              CH.sub.3                                                 CH.sub.3 CH.sub.3     CH.sub.3 CH.sub.3                                        |            |                                               --N------N∠     --N------N∠     C.sub.13 H.sub.22 N.sub.6                                                              32.1                                                                               32.5                   CH.sub.3              CH.sub.3                                                 C.sub.2 H.sub.5       C.sub.2 H.sub.5                                       40.                                                                               --NH--N∠        --NH--N∠        C.sub.15 H.sub.26 N.sub.6                                                              29.0                                                                               29.4                   C.sub.2 H.sub.5       C.sub.2 H.sub.5                                       41.                                            C.sub.23 H.sub.26 N.sub.6                                                              21.8                                                                               21.5                   --NH--NHO             --NH--NHO             C.sub.15 H.sub.22 N.sub.6                                                      O.sub.2 26.4                                                                               26.2                   CH.sub.3              C.sub.2 H.sub.5                                          --NHCH.sub.2 CH.sub.2 N∠                                                                       --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.17 H.sub.30 N.sub.6                                                              26.4                                                                               26.0                   CH.sub.3              C.sub.2 H.sub.5                                          C.sub.2 H.sub.5       C.sub.2 H.sub.5                                          --NHCH.sub.2 CH.sub.2 N∠                                                                       --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.19 H.sub.34 N.sub.6                                                              24.3                                                                               24.5                   C.sub.2 H.sub.5       C.sub.2 H.sub.5                                          CH.sub.3              CH.sub.3                                                 --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              C.sub.17 H.sub.30 N.sub.6                                                              26.4                                                                               26.1                   CH.sub.3              CH.sub.3                                                 --NHCH.sub.2 CH.sub.2 CH.sub.2 --NHO        C.sub.21 H.sub.34 N.sub.6                                                      O.sub.2 20.9                                                                               20.7                                         --NHCH.sub.2 CH.sub.2 CH.sub.2 --NHO                  47.                                            C.sub.23 H.sub.38 N.sub.6                                                              21.1                                                                               21.5                   --NH--OH              --NH--OH              C.sub.7 H.sub.8 N.sub.4                                                        O.sub.2 31.1                                                                               31.6                   CH.sub.3              CH.sub.3                                                 --N∠            --N∠            C.sub.11 H.sub.16 N.sub.4                                                      O.sub.2 23.7                                                                               24.2                   OCH.sub.3             OCH.sub.3                                                CH.sub.2 CH.sub.2 OH  CH.sub.2 CH.sub.2 OH                                  50.                                                                               --N∠            --N∠            C.sub.13 H.sub.20 N.sub.4                                                      O.sub.4 18.9                                                                               19.3                   OCH.sub.3             OCH.sub.3                                             51.                                            C.sub.23 H.sub.24 N.sub.4                                                      O.sub.2 14.4                                                                               15.0                   CH.sub.2 --CH.sub.3   CH.sub.2 --CH.sub.3                                      --N∠            --N∠            C.sub.15 H.sub.24 N.sub.4                                                      O.sub.2 19.2                                                                               19.6                   O--CH.sub.2 --CH.sub.3                                                                               O--CH.sub.2 --CH.sub.3                                   CH.sub.2 CH.sub.2 OH  CH.sub.2 CH.sub.2 OH                                     --N∠            --N∠            C.sub.15 H.sub.24 N.sub.4                                                      O.sub.6 15.7                                                                               16.2                   O--CH.sub.2 CH.sub.2 OH                                                                              O--CH.sub.2 CH.sub.2 OH                               54.                                            C.sub.25 H.sub.28 N.sub.4                                                      O.sub.4 12.5                                                                               12.2                   H.sub.2 C------CH.sub.2                                                                              H.sub.2 C------CH.sub.2                                                                              C.sub.13 H.sub.16 N.sub.4                                                      O.sub.2 21.5                                                                               21.2                   ||  ||                                     --NCH.sub.2           --NCH.sub.2                                              ∠               ∠                                                  O                     O                                                        H.sub.2               H.sub.2                                                  C                     C                                                        ∠               ∠                                                  H.sub.2 CCH.sub.2     H.sub.2 CCH.sub.2     C.sub.15 H.sub.20 N.sub.4                                                      O.sub.2 19.4                                                                               19.8                   ||  ||                                     --NCH.sub.2           --NCH.sub.2                                              ∠               ∠                                                  O                     O                                                        --NH.sub.2            --Cl                  C.sub.7 H.sub.6 ClN.sub.3                                                              25.1                                                                               25.4                   --NH.sub.2            --CN                  C.sub.8 H.sub.6 N.sub.4                                                                35.7                                                                               35.5                   "                     --OH                  C.sub.7 H.sub.7 N.sub.3                                                                28.2                                                                               28.6                60.                                                                               "                     --OCH.sub.3           C.sub.8 H.sub.9 N.sub.3                                                                25.8                                                                               25.2                   "                                           C.sub.13 H.sub.11 N.sub.3                                                      O       18.7                                                                               19.1                   "                     --SH                  C.sub.7 H.sub.7 N.sub.3                                                                25.5                                                                               25.7                   "                     --SC.sub.2 H.sub.5    C.sub.9 H.sub.11 N.sub.3                                                               21.8                                                                               22.3                   --NH.sub.2            --SO.sub.2 --CH.sub.3 C.sub.8 H.sub.9 N.sub.3                                                        O.sub.2 S                                                                              19.9                                                                               20.5                   "                     --NH--CH.sub.3        C.sub.8 H.sub.10 N.sub.4                                                               34.6                                                                               34.2                   "                     --NH--C.sub.2 H.sub.5 C.sub.9 H.sub.12 N.sub.4                                                               31.8                                                                               31.5                   "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.11 H.sub.16 N.sub.4                                                      O       25.5                                                                               25.2                   "                                           C.sub.13 H.sub.12 N.sub.4                                                              25.0                                                                               25.5                   "                                           C.sub.14 H.sub.14 N.sub.4                                                              23.6                                                                               24.1                70.                                                                               "                                           C.sub.16 H.sub.14 N.sub.5                                                              25.4                                                                               25.0                                         CH.sub.3                                                  "                    --N∠            C.sub.9 H.sub.12 N.sub.4                                                               31.8                                                                               31.6                                         CH.sub.3                                                                       CH.sub.3                                                 "                     --N∠            C.sub.10 H.sub.14 ON.sub.4                                                             27.2                                                                               27.7                                         CH.sub.2 CH.sub.2 OH                                                           CH.sub.2 CH.sub.2 OH                                     --NH.sub.2            --N∠            C.sub.11 H.sub.16 O.sub.2                                                      N.sub.4 23.7                                                                               24.2                                         CH.sub.2 CH.sub.2 OH                                     "                     --NHO                 C.sub.11 H.sub.14 ON.sub.4                                                             25.7                                                                               26.2                   "                                           C.sub.12 H.sub.16 N.sub.4                                                              25.9                                                                               26.3                                         CH.sub.3                                                 "                     --NH--N∠        C.sub.9 H.sub.13 N.sub.5                                                               36.6                                                                               36.1                                         CH.sub.3                                                                       C.sub.2 H.sub.5                                          "                     --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.13 H.sub.21 N.sub.5                                                              28.3                                                                               28.1                                         C.sub.2 H.sub.5                                                                CH.sub.2                                                 "                     --NHCH.sub.2 CH.sub.2 N∠|                                                             C.sub.11 H.sub.15 N.sub.5                                                              32.3                                                                               32.2                                         CH.sub.2                                                                       CH.sub.3                                                 "                     --N∠            C.sub.9 H.sub.12 ON.sub.4                                                              29.2                                                                               29.0                                         OCH.sub.3                                                                      C.sub.3 H.sub.7 (iso)                                 80.                                                                               "                     --N∠            C.sub.12 H.sub.18 ON.sub.4                                                             23.9                                                                               23.3                                         O--C.sub.2 H.sub.5                                       --NH--CH.sub.3        --Cl                  C.sub.8 H.sub.8 N.sub.3                                                                23.2                                                                               23.5                   "                     --CN                  C.sub.9 H.sub.8 N.sub.4                                                                32.6                                                                               32.2                   "                     --OH                  C.sub.8 H.sub.9 ON.sub.3                                                               25.8                                                                               26.2                   "                     --OC.sub.2 H.sub.5    C.sub.10 H.sub.13 ON.sub.3                                                             22.0                                                                               22.5                   --NH--CH.sub.3        --SO.sub.2 --C.sub.2 H.sub.5                                                                         C.sub.10 H.sub.13 N.sub.3                                                      O.sub.2 S                                                                              17.6                                                                               17.5                   "                     --NH--C.sub.3 H.sub.7 (n)                                                                            C.sub.11 H.sub.16 N.sub.4                                                              27.5                                                                               27.1                   "                     --NH--C.sub.5 H.sub.11 (iso)                                                                         C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               23.5                   "                                           C.sub.14 H.sub.20 N.sub.4                                                              23.0                                                                               22.5                   "                                           C.sub.15 H.sub.16 N.sub.4                                                              22.2                                                                               22.0                90.                                                                               "                                           C.sub.18 H.sub.16 N.sub.4                                                              19.4                                                                               19.0                   --NH--CH.sub.3        HC------CH            C.sub.13 H.sub.15 N.sub.4                                                      O       23.0                                                                               22.5                                         ∥∥                                                           HCCH--CH.sub.2 --NH--                                                          ∠                                                                        O                                                                              C.sub.2 H.sub.5                                          "                     --N∠            C.sub.12 H.sub.18 N.sub.4                                                              25.7                                                                               26.1                                         C.sub.2 H.sub.5                                                                CH.sub.2 CH.sub.2 CN                                     "                     --N∠            C.sub.13 H.sub.17 N.sub.5                                                      O       27.0                                                                               26.5                                         CH.sub.2 CH.sub.2 OH                                     "                                           C.sub.12 H.sub.16 N.sub.4                                                              25.9                                                                               26.4                   "                     --NHN--CH.sub.3       C.sub.13 H.sub.19 N.sub.5                                                              28.6                                                                               28.2                                         C.sub.2 H.sub.5                                          "                     --NH--N∠        C.sub.12 H.sub.19 N.sub.                                                               30.0                                                                               30.6                                         C.sub.2 H.sub.5                                                                CH.sub.3                                                 --NH--CH.sub.3        --NHCH.sub.2 CH.sub.2 --N∠                                                                     C.sub.12 H.sub.19 N.sub.5                                                              30.0                                                                               30.3                                         CH.sub.3                                                                       CH.sub.2 CH.sub.2 OH                                     "                     --N∠            C.sub.12 H.sub.18 N.sub.4                                                      O.sub.2 22.4                                                                               22.0                                         O--C.sub.2 H.sub.5                                       --NH--C.sub.2 H.sub.5 --Cl                  C.sub.9 H.sub.10 ClN.sub.3                                                             21.5                                                                               21.3                100.                                                                              "                     --CN                  C.sub.10 H.sub.10 N.sub.4                                                              30.1                                                                               30.5                101.                                                                              "                     --OH                  C.sub.9 H.sub.11 N.sub.3                                                               23.7                                                                               23.2                102.                                                                              "                     --OC.sub.3 H.sub.7 (n)                                                                               C.sub.12 H.sub.17 N.sub.3                                                      O       19.2                                                                               19.0                103.                                                                              "                     --SCH.sub.3           C.sub.10 H.sub.13 N.sub.3                                                      S       20.3                                                                               20.7                104.                                                                              "                     --SO.sub.2 --C.sub.3 H.sub.7 (n)                                                                     C.sub.12 H.sub.17 N.sub.3                                                      O.sub.2 S                                                                              15.7                                                                               15.5                105.                                                                              "                     --NH--CH.sub.3        C.sub.10 H.sub.14 N.sub.4                                                              29.5                                                                               29.0                106.                                                                              "                     -- NH--CH.sub.2 --CH.sub.2 --OCH.sub.3                                                               C.sub.12 H.sub.18 N.sub.4                                                      O       23.9                                                                               23.3                107.                                                                              "                     --NH--C.sub.6 H.sub.13 (n)                                                                           C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               21.0                                         CH.sub.3                                              108.                                                                              --NH--C.sub.2 H.sub.5 --N∠            C.sub.11 H.sub.16 N.sub.4                                                              27.5                                                                               27.3                                         CH.sub.3                                              109.                                                                              --NH--C.sub.2 H.sub.5                       C.sub.14 H.sub.20 N.sub.4                                                              23.0                                                                               22.5                                         CH.sub.3                                              110.                                                                              "                     --NH--N∠        C.sub.11 H.sub.17 N.sub.5                                                              32.0                                                                               31.6                                         CH.sub.3                                                                       C.sub.2 H.sub.5                                       111.                                                                              "                     --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.15 H.sub.25 N.sub.5                                                              25.5                                                                               26.0                                         C.sub.2 H.sub.5                                       112.                                                                              "                                           C.sub.23 H.sub.24 N.sub.4                                                      O       15.1                                                                               15.5                113.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                            --OH                  C.sub.10 H.sub.13 N.sub.3                                                      O       22.0                                                                               22.4                114.                                                                              "                     --C--C.sub.3 H.sub.7 (iso)                                                                           C.sub.13 H.sub.19 N.sub.3                                                      O       18.0                                                                               18.5                115.                                                                              "                     --SO.sub.2 --C.sub.5 H.sub.11 (iso)                                                                  C.sub.15 H.sub.23 N.sub.3                                                      O.sub.2 S                                                                              13.6                                                                               13.3                116.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                            --NH--CH.sub.3        C.sub.11 H.sub.16 N.sub.4                                                              27.5                                                                               28.0                117.                                                                              "                     --NH--C.sub.3 H.sub.7 (iso)                                                                          C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               24.5                118.                                                                              "                                           C.sub.16 H.sub.24 N.sub.4                                                              20.6                                                                               21.0                119.                                                                              "                                           C.sub.16 H.sub.18 N.sub.4                                                              21.1                                                                               21.5                                         CH.sub.3                                              120.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                            --N∠            C.sub.12 H.sub.18 N.sub.4                                                              25.7                                                                               26.0                                         CH.sub.3                                              121.                                                                              "                                           C.sub.19 H.sub.24 N.sub.4                                                      O       17.3                                                                               17.5                122.                                                                              "                     --NH--NHO             C.sub.14 H.sub.21 N.sub.5                                                      O       25.5                                                                               26.1                                         CH.sub.3                                              123.                                                                              "                     --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.14 H.sub.23 N.sub.5                                                              26.8                                                                               26.4                                         CH.sub. 3                                                                      CH.sub.3                                              124.                                                                              --NH--C.sub.3 H.sub.7 (n)                                                                            --N∠            C.sub.12 H.sub.18 N.sub.4                                                      O       23.9                                                                               23.2                                         OCH.sub.3                                             125.                                                                              --NH--C.sub.3 H.sub.7 (iso)                                                                          --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.14 H.sub.22 N.sub.4                                                      O       21.4                                                                               21.0                                         C.sub.2 H.sub.5                                       126.                                                                              "                     --N∠            C.sub.14 H.sub.22 N.sub.4                                                              22.8                                                                               23.0                                         C.sub.2 H.sub.5                                       127.                                                                              --NH--C.sub.4 H.sub.9 (n)                                                                            --Cl                  C.sub.11 H.sub.14 ClN.sub.3                                                    1       18.8                                                                               19.0                128.                                                                              "                     --OH                  C.sub.11 H.sub.15 N.sub.3                                                      O       20.5                                                                               21.0                129.                                                                              "                     --O--C.sub.4 H.sub.9 (n)                                                                             C.sub.15 H.sub.23 N.sub.3                                                      O       16.1                                                                               16.4                130.                                                                              "                     --NH--CH.sub.3        C.sub.12 H.sub.18 N.sub.4                                                              25.7                                                                               25.0                131.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.13 H.sub.20 N.sub.4                                                      O       22.6                                                                               23.0                                         CH.sub.3                                              132.                                                                              --NH--C.sub.4 H.sub.9 (iso)                                                                          --N∠            C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               23.8                                         CH.sub.3                                              133.                                                                              --NH--C.sub.4 H.sub.9 (iso)                                                                          --NHN--CH.sub.3       C.sub.16 H.sub.25 N.sub.5                                                              24.4                                                                               24.1                                         C.sub.2 H.sub.5                                       134.                                                                              --NH--C.sub.4 H.sub.9 (sek)                                                                          --N∠            C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               22.0                                         C.sub.2 H.sub.5                                                                CH.sub.3                                              135.                                                                              "                     --NH--N∠        C.sub.13 H.sub.21 N.sub.5                                                              28.3                                                                               28.5                                         CH.sub.3                                                                       CH.sub.2 CH.sub.2 OH                                  136.                                                                              "                     --N∠            C.sub.16 H.sub.26 N.sub.4                                                      O.sub.2 18.3                                                                               18.7                                         O--CH.sub.2 CH.sub.2 CH.sub.3                         137.                                                                              --NH--C.sub.4 H.sub.9 (tert)                                                                         --NH--C.sub.2 H.sub.5 C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               24.5                138.                                                                              "                     --NH--CH.sub.2 --CH.sub.2 --CN                                                                       C.sub.14 H.sub.19 N.sub.5                                                              27.2                                                                               27.5                139.                                                                              --NH--C.sub.5 H.sub.11 (n)                                                                           --NH--CH.sub.3        C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               24.5                                         CH.sub.3                                              140.                                                                              "                     --N∠            C.sub.14                                                                               22.8b.22 N.sub.4                                                                   23.0                                         CH.sub.3                                              141.                                                                              --NH--C.sub.5 H.sub.11 (n)                  C.sub.18 H.sub.23 N.sub.5                                                              22.7                                                                               23.2                                         CH.sub.3                                              142.                                                                              --NH--C.sub.5 H.sub.11 (iso)                                                                         --NH--N∠        C.sub.14 H.sub.23 N.sub.5                                                              26.8                                                                               27.2                                         CH.sub.3                                                                       C.sub.2 H.sub.5                                       143.                                                                              --NH--C.sub.6 H.sub.13 (n)                                                                           --N∠            C.sub.17 H.sub.28 N.sub.4                                                              19.4                                                                               19.0                                         C.sub.2 H.sub.5                                       144.                                                                              --NH--C.sub.6 H.sub.13 (n)                                                                           --NHO                 C.sub.12 H.sub.26 N.sub.4                                                      O       18.5                                                                               18.9                                         CH.sub.3                                              145.                                                                              "                     --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.17 H.sub.29 N.sub.5                                                              23.1                                                                               23.3                                         CH.sub.3                                              146.                                                                              --NHCH.sub.2 CH.sub.2 OH                                                                             --NH--CH.sub.3        C.sub.10 H.sub.14 N.sub.4                                                      O       27.2                                                                               27.5                147.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2 21.2                                                                               21.5                                         CH.sub.3                                              148.                                                                              "                     --N∠            C.sub.11 H.sub.16 N.sub.4                                                      O       25.5                                                                               26.0                                         CH.sub.3                                              149.                                                                              "                     --NHO                 C.sub.13 H.sub.18 N.sub.4                                                      O.sub.2 21.4                                                                               21.7                150.                                                                              --NHCH.sub.2 CH.sub.2 OH                    C.sub.14 H.sub.20 N.sub.4                                                      O       21.5                                                                               21.8                                         CH.sub.2                                              151.                                                                              "                     --NHCH.sub.2 CH.sub.2 N∠|                                                             C.sub.13 H.sub.19 N.sub.5                                                      O       26.8                                                                               27.2                                         CH.sub.2                                              152.                                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                      --NH--CH.sub.3        C.sub.11 H.sub.16 N.sub.4                                                      O       25.5                                                                               25.8                                         CH.sub.3                                              153.                                                                              "                     --N∠            C.sub.12 H.sub.18 N.sub.4                                                      O       23.9                                                                               24.3                                         CH.sub.3                                                                       C.sub.2 H.sub.5                                       154.                     --N∠            C.sub.19 H.sub.24 N.sub.4                                                      O       17.3                                                                               17.5                                         C.sub.2 H.sub.5                                       155.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 CN                                                                    --NH--C.sub.2 H.sub.5 C.sub.13 H.sub.17 N.sub.5                                                              28.8                                                                               28.2                                         CH.sub.3                                              156.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 CN                                                                    --N∠            C.sub.14 H.sub.19 N.sub.5                                                      O       25.6                                                                               26.0                                         CH.sub.2 CH.sub.2 OH                                                           C.sub.2 H.sub.5                                       157.                                                                              "                     --N∠            C.sub.15 H.sub.21 N.sub.5                                                              25.8                                                                               26.3                                         C.sub.2 H.sub.5                                       158.                                                                              "                                           C.sub.18 H.sub.20 N.sub.6                                                              26.2                                                                               27.0                159.                                           C.sub.27 H.sub.20 N.sub.4                                                              14.0                                                                               13.5                160.                                                                              --NH--C.sub.2 H.sub.5                       C.sub.15 H.sub.22 N.sub.4                                                              21.7                                                                               22.2                161.                                                                              "                                           C.sub.17 H.sub.20 N.sub.4                                                              20.0                                                                               20.4                162.                                                                              "                                           C.sub.16 H.sub.18 N.sub.4                                                              21.1                                                                               21.5                163.                                                                              --NH--C.sub.4 H.sub.9 (n)                   C.sub.18 H.sub.22 N.sub.4                                                      O       18.1                                                                               18.6                164.                                           C.sub.20 H.sub.21 N.sub.5                                                              21.1                                                                               21.7                165.                                                                              "                     --NH.sub.2            C.sub.13 H.sub.18 N.sub.4                                                              24.3                                                                               24.5                166.                                                                              "                     --NH-- CH.sub.3       C.sub.14 H.sub.20 N.sub.4                                                              23.0                                                                               23.5                167.                     --NH--CH.sub.2 --CH=CH.sub.2                                                                         C.sub.16 H.sub.22 N.sub.4                                                              20.7                                                                               21.0                168.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.17 H.sub.26 N.sub.4                                                      O       19.2                                                                               19.5                                         CH.sub.3                                              169.                                                                              "                     --N∠            C.sub.15 H.sub.22 N.sub.4                                                              21.7                                                                               22.2                                         CH.sub.3                                              170.                                                                              "                     --NH--NHN--CH.sub.3   C.sub.18 H.sub.28 N.sub.6                                                              25.6                                                                               26.0                                         CH.sub.3                                              171.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              C.sub.19 H.sub.29 N.sub.5                                                              22.2                                                                               22.5                                         CH.sub.3                                                                       H.sub.2                                                                        C                                                                              ∠                                               172.                     H.sub.2 CCH.sub.2     C.sub.17 H.sub.24 N.sub.4                                                      O       18.7                                                                               19.1                                         ||                                                           --NCH.sub.2                                                                    ∠                                                                        O                                                     173.                     --NH.sub.2            C.sub.14 H.sub.14 N.sub.4                                                              23.5                                                                               24.0                174.                                                                              "                     --NH--C.sub.2 H.sub.5 C.sub.16 H.sub.18 N.sub.4                                                              21.2                                                                               22.0                                         C.sub.2 H.sub.5                                       175.                                                                              "                     --N∠            C.sub.18 N.sub.22 N.sub.4                                                              19.0                                                                               19.3                                         C.sub.2 H.sub.5                                       176.                                                                              "                     --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                      C.sub.17 H.sub.20 N.sub.4                                                      O       18.9                                                                               18.4                                         C.sub.2 H.sub.5                                       177.                                                                              "                     --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.20 H.sub.27 N.sub.5                                                              20.8                                                                               21.4                                         C.sub.2 H.sub.5                                       178.                                           C.sub.21 H.sub.21 N.sub.5                                                              20.4                                                                               20.6                179.                                           C.sub.22 H.sub.22 N.sub.4                                                      O       15.6                                                                               16.0                180.                     --NH--CH.sub.3        C.sub.18 H.sub.18 N.sub.4                                                              21.1                                                                               21.5                                         CH.sub.3                                              181.                                                                              "                     --N∠            C.sub.17 H.sub.20 N.sub.4                                                              20.0                                                                               20.5                                         CH.sub.3                                              182.                                                                              "                     --NHO                 C.sub.17 H.sub.23 N.sub.4                                                      O       18.7                                                                               19.0                183.                     -- NH.sub.2           C.sub.13 H.sub.12 N.sub.4                                                              25.0                                                                               24.7                184.                                                                              "                     --NH--CH.sub.3        C.sub.14 H.sub.14 N.sub.4                                                              23.6                                                                               24.2                185.                                                                              "                     --NH--C.sub.3 H.sub.7 (n)                                                                            C.sub.16 H.sub.18 N.sub.4                                                              21.1                                                                               21.3                186.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.15 H.sub.16 N.sub.4                                                      O       20.9                                                                               21.5                                         CH.sub.3                                              187.                     --N∠            C.sub.15 H.sub.16 N.sub.4                                                              22.2                                                                               22.0                                         CH.sub.3                                                                       CH.sub.2 CH.sub.2 CN                                  188.                                                                              "                     --N∠            C.sub.19 H.sub.18 N.sub.6                                                              25.5                                                                               25.9                                         CH.sub.2 CH.sub.2 CN                                  189.                     --NHO                 C.sub.17 H.sub.18 N.sub.4                                                      O       19.1                                                                               19.7                                         C.sub.2 H.sub.5                                       190.                                                                              "                     --NH--N∠        C.sub.17 H.sub.21 N.sub.5                                                              23.7                                                                               24.3                                         C.sub.2 H.sub.5                                                                CH.sub.3                                              191.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              C.sub.18 H.sub.23 N.sub.5                                                              22.7                                                                               22.3                                         CH.sub.3                                                                       CH.sub.3                                              192.                                                                              "                     --N∠            C.sub.15 H.sub.16 N.sub.4                                                      O       20.9                                                                               21.4                                         O--CH.sub.3                                           193.                     --NH--CH.sub.3        C.sub.14 H.sub.13 ClN.sub.4                                                    .       20.6                                                                               20.2                194.                     --NH--CH.sub.3        C.sub.15 H.sub.16 N.sub.4                                                              22.2                                                                               22.8                                         CH.sub.3                                              195.                     --N∠            C.sub.17 H.sub.20 N.sub.4                                                              20.0                                                                               20.5                                         CH.sub.3                                              196.                     "                     C.sub.16 H.sub.18 N.sub.4                                                      O       19.9                                                                               20.3                197.                                                                              HC------CH            --NH--CH.sub.3        C.sub.13 H.sub.14 N.sub.4                                                      O       23.1                                                                               23.5                   ∥∥                                                           --NH--CH.sub.2 --CCH                                                           ∠                                                                        O                                                                                                    CH.sub.3                                              198.                                                                              "                     --N∠            C.sub.14 H.sub.16 N.sub.4                                                      O       21.9                                                                               21.5                                         CH.sub.3                                                                       C.sub.2 H.sub.5                                       199.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              C.sub. 19 H.sub.27 N.sub.5                                                     O       20.5                                                                               20.9                                         C.sub.2 H.sub.5                                       200.                     --NH--CH.sub.3        C.sub.14 H.sub.15 N.sub.5                                                              27.7                                                                               27.2                201.                     --NH--CH.sub.3        C.sub.14 H.sub.15 N.sub.5                                                              27.7                                                                               28.2                202.                     --NH--CH.sub.3        C.sub.15 H.sub.17 N.sub.5                                                              26.2                                                                               26.0                203.                     --NH--CH.sub.3        C.sub.15 H.sub.17 N.sub.5                                                              26.2.                                                                              26.6                204.                                                                              --NH--HC------CH.sub.2                                                                               --NH--CH.sub.3        C.sub.12 H.sub.16 N.sub.4                                                      O.sub.2 S                                                                              20.0                                                                               20.5                   ||                                                           H.sub.2 CCH.sub.2                                                              ∠                                                                        S                                                                              O.sub.2                                                                                              CH.sub.3                                              205.                                                                              "                     --N∠            C.sub.13 H.sub.18 N.sub.4                                                      O.sub.2 S                                                                              19.0                                                                               18.7                                         CH.sub.3                                              206.                                                                              "                     --NHO                 C.sub.15 H.sub.20 N.sub.4                                                      O.sub.3 S                                                                              16.7                                                                               17.1                                         CH.sub.3                                              207.                                                                              "                     --NH--N∠        C.sub.13 H.sub. 19 N.sub.5                                                     O.sub.2 S                                                                              22.7                                                                               22.2                                         CH.sub.3                                              208.                     --NH--CH.sub.3        C.sub.17 H.sub.17 N.sub.5                                                              24.1                                                                               24.5                                         CH.sub.3                                              209.                                                                              "                     --N∠            C.sub.18 H.sub.19 N.sub.5                                                              23.0                                                                               23.5                                         CH.sub.3                                              210.                                                                              "                     --NHO                 C.sub.20 H.sub.21 N.sub.5                                                      O       20.2                                                                               20.5                211.                     --Cl                  C.sub.13 H.sub.16 ClN.sub.3                                                            16.9                                                                               16.5                212.                                                                              "                     --OH                  C.sub.13 H.sub.17 N.sub.3                                                      O       18.2                                                                               18.6                213.                                                                              "                     --OCH.sub.3           C.sub.14 H.sub.19 N.sub.3                                                      O       17.1                                                                               17.6                214.                                                                              "                     --CN                  C.sub.14 H.sub.16 N.sub.4                                                              25.0                                                                               25.3                215.                                                                              "                                           C.sub.20 H.sub.23 N.sub.3                                                      O.sub.2 S                                                                              11.4                                                                               11.2                216.                     --Cl                  C.sub.14 H.sub.12 ClN.sub.3                                                            16.3                                                                               16.0                217.                                                                              "                     --OH                  C.sub.14 H.sub.13 N.sub.3                                                      O       17.6                                                                               18.0                218.                                                                              "                     --O--CH.sub.3         C.sub. 15 H.sub.15 N.sub.3                                                     O       16.6                                                                               16.0                219.                                                                              "                     --S--C.sub.4 H.sub.9 (n)                                                                             C.sub.18 H.sub.21 N.sub.3                                                      S       21.5                                                                               21.8                220.                     --Cl                  C.sub.13 H.sub.10 ClN.sub.3                                                            17.3                                                                               17.0                221.                     --CN                  C.sub.14 H.sub.10 N.sub.4                                                              23.9                                                                               24.3                222.                                                                              "                     --OH                  C.sub.13 H.sub.11 N.sub.3                                                      O       18.7                                                                               18.5                223.                                                                              "                     --OCH.sub.3           C.sub.14 H.sub.13 N.sub.3                                                      O       17.6                                                                               17.3                224.                                                                              "                     --SCH.sub.3           C.sub.14 H.sub.13 N.sub.3                                                      S       16.5                                                                               16.0                   CH.sub.3                                                                    225.                                                                              --N∠            --Cl                  C.sub.9 H.sub.10 ClN.sub.3                                                             21.5                                                                               21.0                   CH.sub.3                                                                    226.                                                                              "                     --CN                  C.sub.10 H.sub.10 N.sub.4                                                              30.1                                                                               30.5                227.                                                                              "                     --OH                  C.sub.9 H.sub.11 N.sub.3                                                               23.7                                                                               23.4                228.                                                                              "                     --OCH.sub.3           C.sub.10 H.sub.13 N.sub.3                                                      O       22.0                                                                               22.3                229.                                                                              "                     --SO.sub.2 --C.sub.2 H.sub.5                                                                         C.sub.11 H.sub.15 N.sub.3                                                      O.sub.2 S                                                                              16.6                                                                               17.0                230.                                                                              "                     --NH--CH.sub.3        C.sub.10 H.sub.14 N.sub.4                                                              29.5                                                                               29.1                231.                                                                              "                     --NH--C.sub.3 H.sub.7 (n)                                                                            C.sub.12 H.sub.18 N.sub.4                                                              25.7                                                                               26.2                232.                                                                              "                     --NH--C.sub.6 H.sub.13 (n)                                                                           C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               21.8                   CH.sub.3                                                                    233.                                                                              --N∠                                  C.sub.15 H.sub.22 N.sub.4                                                              21.7                                                                               21.5                   CH.sub.3                                                                    234.                                                                              "                                           C.sub.16 H.sub.18 N.sub.4                                                              21.1                                                                               20.7                235.                                                                              "                                           C.sub.15 H.sub.16 N.sub.4                                                              22.2                                                                               22.6                236.                                                                              "                                           C.sub.19 H.sub.18 N.sub.4                                                              18.5                                                                               18.9                237.                                                                              "                     HC------CH            C.sub.14 H.sub.16 N.sub.4                                                      O       21.9                                                                               21.5                                         ∥∥                                                           HCC--CH.sub.2 --NH--                                                           ∠                                                                        O                                                                              C.sub.2 H.sub.5                                       238.                                                                              "                     --N∠            C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               23.8                                         C.sub.2 H.sub.5                                          CH.sub.3              CH.sub.2 CH.sub.2 CN                                  239.                                                                              --N∠            --N∠            C.sub.14 H.sub.19 N.sub.5                                                      O       25.6                                                                               26.0                   CH.sub.3              CH.sub.2 CH.sub.2 OH                                  240.                                                                              "                                           C.sub.13 H.sub.18 N.sub.4                                                              24.3                                                                               24.5                   CH.sub.3                                                                    241.                                                                              --N∠            --NHN--CH.sub.3       C.sub.14 H.sub.21 N.sub.5                                                              27.0                                                                               27.4                   CH.sub.3                                                                                             C.sub.2 H.sub.5                                       242.                                                                              "                     --NH--N∠        C.sub.13 H.sub.21 N.sub.5                                                              28.3                                                                               27.9                                         C.sub.2 H.sub.5                                                                CH.sub.3                                              243.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              C.sub.14 H.sub.23 N.sub.5                                                              26.8                                                                               26.6                                         CH.sub.3                                                                       CH.sub.2 CH.sub.2 OH                                  244.                                                                              "                     --N∠            C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2 21.2                                                                               21.6                                         O--C.sub.2 H.sub.5                                       C.sub.2 H.sub.5                                                             245.                                                                              --N∠            --Cl                  C.sub.11 H.sub.14 ClN.sub.3                                                            18.8                                                                               18.5                   C.sub.2 H.sub.5                                                             246.                                                                              "                     --CN                  C.sub.12 H.sub.14 N.sub.                                                               26.2                                                                               26.6                247.                                                                              "                     --OH                  C.sub.11 H.sub.15 N.sub.3                                                      O       20.5                                                                               21.0                248.                                                                              "                     --OCH.sub.3           C.sub.12 H.sub.17 N.sub.3                                                      O       19.2                                                                               19.0                249.                                                                              "                     --SC.sub.2 H.sub.5    C.sub.13 H.sub.19 N.sub.3                                                      S       16.8                                                                               17.2                   C.sub.2 H.sub.5                                                             250.                                                                              --N∠            --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                                     C.sub.15 H.sub.23 N.sub.3                                                      SO.sub.2                                                                               13.6                                                                               13.5                   C.sub.2 H.sub.5                                                                C.sub.2 H.sub.5                                                             251.                                                                              --N∠            --NH--CH.sub.3        C.sub.12 H.sub.17 N.sub.4                                                              25.7                                                                               25.5                   C.sub.2 H.sub.5                                                             252.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.15 H.sub.24 N.sub.4                                                      O       20.3                                                                               20.0                253.                                                                              "                                           C.sub.17 H.sub.25 N.sub.4                                                              19.6                                                                               19.5                254.                                                                              "                                           C.sub.18 H.sub.22 N.sub.4                                                              19.0                                                                               19.4                255.                                                                              "                                           C.sub.17 H.sub.20 N.sub.4                                                              20.0                                                                               20.2                256.                                                                              "                                           C.sub.16 H.sub.24 N.sub.                                                               20.6                                                                               21.0                                         CH.sub.3                                              257.                                                                              "                     --NH--N∠        C.sub.13 H.sub.21 N.sub.5                                                              28.3                                                                               28.0                                         CH.sub.3                                                                       CH.sub.3                                              258.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH.sub.2 N∠                                                              C.sub.16 H.sub.27 N.sub.5                                                              24.2                                                                               24.5                                         CH.sub.3                                                 C.sub.2 H.sub.5       CH.sub.3                                              259.                                                                              --N∠            --N∠            C.sub.13 H.sub.20 N.sub.4                                                      O       22.6                                                                               22.2                   C.sub.2 H.sub.5       OCH.sub.3                                                CH.sub.2 CH.sub.2 CN                                                        260.                                                                              --N∠            --OCH.sub.3           C.sub.13 H.sub.16 N.sub.4                                                      O.sub.2 21.5                                                                               21.3                   CH.sub.2 CH.sub.2 OH                                                        261.                                                                              "                     --NHO                 C.sub.16 H.sub.21 N.sub.5                                                      O.sub.2 22.2                                                                               22.6                   CH.sub.2 CH.sub.2 OH                                                        262.                                                                              --N∠            --NH.sub.2            C.sub.11 H.sub.16 N.sub.4                                                      O.sub.2 23.7                                                                               23.4                   CH.sub.2 CH.sub.2 OH                                                           CH.sub.2 CH.sub.2 OH  CH.sub.3                                              263.                                                                              --N∠            --N∠            C.sub.13 H.sub. 20 N.sub.4                                                     O.sub.2 21.2                                                                               21.5                   CH.sub.2 CH.sub.2 OH  CH.sub.3                                              264.                                                                              "                                           C.sub.17 H.sub.20 N.sub.4                                                      O.sub.2 17.9                                                                               18.2                   CH.sub.2 CH.sub.2 CN                                                        265.                                                                              --N∠            --OCH.sub.3           C.sub.14 H.sub.15 N.sub.5                                                      O       26.0                                                                               26.3                   CH.sub.2 CH.sub.2 CN                                                                                 CH.sub.3                                              266.                                                                              "                     --N∠            C.sub.15 H.sub.18 N.sub.6                                                              29.8                                                                               29.5                   CH.sub.3                                                                    267.                                                                              --N∠            --NH.sub.2            C.sub.10 H.sub.14 N.sub.4                                                      O       27.2                                                                               27.5                   CH.sub.2 CH.sub.2 OH                                                        268.                                                                              "                     --NH--CH.sub.3        C.sub.11 H.sub.16 N.sub.4                                                      O       25.5                                                                               25.8                269.                                                                              "                                           C.sub.16 H.sub.24 N.sub.5                                                      O       23.2                                                                               23.7                270.                                                                              "                                           C.sub.16 H.sub.18 N.sub.4                                                      O       19.9                                                                               19.5                                         CH.sub.3                                              271.                                                                              "                     --NH--N∠        C.sub.12 H.sub.19 N.sub.5                                                      O       28.1                                                                               27.8                                         CH.sub.3                                                 C.sub.3 H.sub.7 (iso)                                                       272.                                                                              --N∠            --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.16 H.sub. 26 N.sub.4                                                     O.sub.2 13.8                                                                               14.2                   CH.sub.2 CH.sub.2 OH                                                           C.sub.4 H.sub.9 (n)                                                         273.                                                                              --N∠            --NH--CH.sub.3        C.sub.14 H.sub.22 N.sub.4                                                      O       21.4                                                                               21.0                   CH.sub.2 CH.sub.2 OH                                                           C.sub.4 H.sub.9 (n)                                                         274.                                                                              --N∠            --NHO                 C.sub.17 H.sub.26 N.sub.4                                                      O.sub.2 17.6                                                                               18.0                   CH.sub.2 CH.sub.2 OH                                                           C.sub.4 H.sub.9 (n)   CH.sub.3                                              275.                                                                              --N∠            --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.17 H.sub.29 N.sub.5                                                      O       21.9                                                                               21.7                   CH.sub.2 CH.sub.2 OH  CH.sub.3                                              276.                     --NH--CH.sub.3        C.sub.16 H.sub.23 N.sub.4                                                      O       19.4                                                                               19.0                277.                                           C.sub.21 H.sub.32 N.sub.4                                                      O       15.7                                                                               16.3                278.                     --NH.sub.2            C.sub.16 H.sub.18 N.sub.4                                                      O       19.9                                                                               19.5                279.                     --NH--CH.sub.3        C.sub.17 H.sub.20 N.sub.4                                                      O       18.9                                                                               19.5                280.                                                                              "                                           C.sub.23 H.sub.25 N.sub.5                                                      O       18.1                                                                               18.5                   C.sub.3 H.sub.7 (n)                                                         281.                                                                              --N∠            --Cl                  C.sub.13 H.sub.18 ClN.sub.3                                                            16.7                                                                               16.5                   C.sub.3 H.sub.7 (n)                                                         282.                                                                              "                     --NH.sub.2            C.sub.13 H.sub.20 N.sub.4                                                              24.1                                                                               24.5                283.                                                                              "                     --CN                  C.sub.14 H.sub.18 N.sub.4                                                              23.1                                                                               23.7                   C.sub.3 H.sub.7 (n)                                                         284.                                                                              --N∠            --OH                  C.sub.13 H.sub.19 N.sub.3                                                      O       18.0                                                                               18.4                   C.sub.3 H.sub.7 (n)                                                         285.                                                                              "                     --OCH.sub.3           C.sub.14 H.sub.21 N.sub.3                                                      O       17.0                                                                               17.5                286.                                                                              "                     --SO.sub.2 --CH.sub.3 C.sub.14 H.sub.21 N.sub.3                                                      O.sub.2 S                                                                              14.2                                                                               13.8                287.                                                                              "                     --NH--CH.sub.3        C.sub.14 H.sub.22 N.sub.4                                                              22.8                                                                               23.2                288.                                                                              "                     --NH--C.sub.3 H.sub.7 (n)                                                                            C.sub.16 H.sub.26 N.sub.4                                                              20.5                                                                               21.0                289.                                                                              "                                           C.sub.19 H.sub.30 N.sub.4                                                              17.8                                                                               17.5                290.                                                                              "                                           C.sub.19 H.sub.24 N.sub.4                                                              18.2                                                                               18.5                                         CH.sub.3                                              291.                                                                              "                     --N∠            C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               20.8                                         CH.sub.3                                              292.                                                                              "                     --NH--NHO             C.sub.17 H.sub.27 N.sub.5                                                      O       22.1                                                                               22.5                   C.sub.3 H.sub.7 (n)   CH.sub.3                                              293.                                                                              --N∠            --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.17 H.sub.29 N.sub.5                                                              23.1                                                                               23.6                   C.sub.3 H.sub.7 (n)   CH.sub.3                                                                       CH.sub.3                                              294.                                                                              "                     --N∠            C.sub.15 H.sub.23 N.sub.4                                                      O       20.3                                                                               20.0                                         OCH.sub.3                                                C.sub.3 H.sub.7 (iso)                                                       295.                                                                              --N∠            --NH.sub.2            C.sub.13 H.sub.20 N.sub.4                                                              24.2                                                                               24.6                   C.sub.3 H.sub.7 (iso)                                                       296.                                                                              "                     --OH                  C.sub.13 H.sub.19 N.sub.3                                                      O       18.0                                                                               18.5                   C.sub.3 H.sub.7 (iso)                                                       297.                                                                              --N∠            --NH--CH.sub.3        C.sub.14 H.sub.22 N.sub.4                                                              22.8                                                                               22.5                   C.sub.3 H.sub.7 (iso)                                                       298.                                                                              "                                           C.sub.18 H.sub.28 N.sub.4                                                              18.7                                                                               19.1                   C.sub.4 H.sub.9 (n)                                                         299.                                                                              --N∠            --Cl                  C.sub.15 H.sub.22 ClN.sub.3                                                            15.0                                                                               15.4                   C.sub.4 H.sub.9 (n)                                                         300.                                                                              "                     --CN                  C.sub.16 H.sub.22 N.sub.4                                                              20.7                                                                               21.0                   C.sub.4 H.sub.9 (n)                                                         301.                                                                              --N∠            --OH                  C.sub.15 H.sub.23 N.sub.3                                                      O       16.1                                                                               16.5                   C.sub.4 H.sub.9 (n)                                                         302.                                                                              "                     --OCH.sub.3           C.sub.16 H.sub.25 N.sub.3                                                      O       15.3                                                                               15.0                303.                                                                              "                     --NH--CH.sub.3        C.sub.16 H.sub.26 N.sub.4                                                              20.4                                                                               20.8                304.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.17 H.sub.28 N.sub.4                                                      O       18.4                                                                               18.1                305.                                                                              "                                           C.sub.21 H.sub.34 N.sub.4                                                              16.4                                                                               16.8                306.                                                                              "                     --NHO                 C.sub.19 H.sub.30 N.sub.4                                                      O       17.0                                                                               17.3                                         CH.sub.3                                              307.                                                                              "                     --NH--N∠        C.sub.17 H.sub.29 N.sub.5                                                              23.1                                                                               23.5                                         CH.sub.3                                              308.                                                                              "                     --NH--NHO             C.sub.19 H.sub.31 N.sub.5                                                      O       20.3                                                                               21.0                   C.sub.4 H.sub.9 (iso)                                                       309.                                                                              --N∠            --NH.sub.2            C.sub.15 H.sub.24 N.sub.4                                                              21.5                                                                               21.9                   C.sub.4 H.sub.9 (iso)                                                       310.                                                                              "                     --NH--CH.sub.3        C.sub.16 H.sub.26 N.sub.4                                                              20.4                                                                               20.6                   C.sub.4 H.sub.9 (iso)                                                       311.                                                                              --N∠            --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.17 H.sub.28 N.sub.4                                                      O       18.4                                                                               18.5                   C.sub.4 H.sub.9 (iso)                                                          C.sub.4 H.sub.9 (iso) CH.sub.3                                              312.                                                                              --N∠            --NHCH.sub.2 CH.sub.2 N∠                                                                       C.sub.19 H.sub.33 N.sub.5                                                              21.1                                                                               21.5                   C.sub.4 H.sub.9 (iso) CH.sub.3                                                 C.sub.5 H.sub.11 (n)                                                        313.                                                                              --N∠            --NH.sub.2            C.sub.17 H.sub.28 N.sub.4                                                              19.4                                                                               20.0                   C.sub.5 H.sub.11 (n)                                                        314.                                                                              "                     --NH--CH.sub.3        C.sub.18 H.sub.30 N.sub.4                                                              18.5                                                                               18.2                315.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.19 H.sub.32 N.sub.4                                                      O       16.9                                                                               17.5                   C.sub.6 H.sub.13 (n)                                                        316.                                                                              --N∠            --NH.sub.2            C.sub.19 H.sub.32 N.sub.4                                                              17.7                                                                               18.0                   C.sub.6 H.sub.13 (n)                                                        317.                                                                              "                     --NH--CH.sub.3        C.sub.20 H.sub.34 N.sub.4                                                              17.0                                                                               16.7                318.                                                                              "                                           C.sub.25 H.sub.36 N.sub.4                                                              14.3                                                                               14.7                319.                                                                              --NHO                 --NH.sub.2            C.sub.11 H.sub.14 N.sub.4                                                      O       25.7                                                                               26.2                320.                                                                              "                     --OH                  C.sub.11 H.sub.13 N.sub.3                                                      O.sub.2 19.2                                                                               19.5                321.                                                                              "                     --NH--CH.sub.3        C.sub.12 H.sub.16 N.sub.4                                                      O       24.1                                                                               24.5                                         C.sub.2 H.sub.5                                       322.                                                                              --NHO                 --N∠            C.sub.15 H.sub.22 N.sub.4                                                      O       20.4                                                                               21.0                                         C.sub.2 H.sub.5                                       323.                     --NH.sub.2            C.sub.11 H.sub.14 N.sub.4                                                              27.7                                                                               28.0                324.                                                                              "                     --NH--CH.sub.3        C.sub.12 H.sub.16 N.sub.4                                                              25.9                                                                               25.7                                         CH.sub.3                                              325.                                                                              "                     --N∠            C.sub.13 H.sub.18 N.sub.4                                                              24.3                                                                               25.0                                         CH.sub.3                                              326.                     --OH                  C.sub.12 H.sub.15 N.sub.3                                                      O       19.3                                                                               19.5                327.                                                                              "                     --NH.sub.2            C.sub.12 H.sub.16 N.sub.4                                                              25.9                                                                               25.5                328.                                                                              "                     --NH--CH.sub.3        C.sub.13 H.sub.18 N.sub.4                                                              24.3                                                                               24.7                329.                                                                              "                     --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.16 H.sub.24 N.sub.4                                                      O       19.4                                                                               19.5                                         CH.sub.3                                              330.                                                                              "                     --N∠            C.sub.14 H.sub.20 N.sub.4                                                              22.9                                                                               23.0                                         CH.sub.3                                              331.                                                                              "                                           C.sub.18 H.sub.26 N.sub.4                                                              18.8                                                                               18.5                332.                                           C.sub.18 H.sub.20 N.sub.4                                                              19.2                                                                               19.2                333.                                                                              --NHN--CH.sub.3       --NH.sub.2            C.sub.12 H.sub.17 N.sub.5                                                              30.4                                                                               30.6                334.                                                                              "                     --NH--CH.sub.3        C.sub.13 H.sub.19 N.sub.5                                                              28.5                                                                               28.7                                         CH.sub.3                                              335.                                                                              "                     --N∠            C.sub.14 H.sub.21 N.sub.5                                                              27.0                                                                               27.5                                         CH.sub.3                                              336.                                                                              --NHN--C.sub.2 H.sub.5                                                                               --NH--CH.sub.3        C.sub.14 H.sub.21 N.sub.5                                                              27.0                                                                               27.3                   CH.sub.3 CH.sub.3                                                              |                                                                  337.                                                                              --N------N∠     --NH--CH.sub.3        C.sub.11 H.sub.17 N.sub.5                                                              32.0                                                                               32.3                   CH.sub.3                                                                    338.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.12 H.sub.19 N.sub.5                                                      O       28.1                                                                               28.0                   CH.sub.3                                                                    339.                                                                              --NH--N∠        --NH.sub.2            C.sub.9 H.sub.13 N.sub.5                                                               36.7                                                                               37.0                   CH.sub.3                                                                    340.                                                                              "                     --NH--CH.sub.3        C.sub.10 H.sub.15 N.sub.5                                                              34.1                                                                               34.5                   C.sub.2 H.sub.5       CH.sub.3                                              341.                                                                              --NH--N∠        --N∠            C.sub.13 H.sub.21 N.sub.5                                                              28.4                                                                               29.0                   C.sub.2 H.sub.5       CH.sub.3                                                                       CH.sub.3                                              342.                                                                              "                     --N∠            C.sub.14 H.sub.23 N.sub.5                                                      O       25.3                                                                               25.5                                         CH.sub.2 CH.sub.2 OH                                  343.                                                                              "                                           C.sub.17 H.sub.21 N.sub.5                                                              23.8                                                                               24.0                344.                     --NH--CH.sub.3        C.sub.15 H.sub.17 N.sub.5                                                              26.2                                                                               26.6                                         CH.sub.3                                              345.                                                                              "                     --N∠            C.sub.16 H.sub.19 N.sub.5                                                              24.9                                                                               25.5                346.                     --NH--CH.sub.3        C.sub.13 H.sub.17 N.sub.5                                                              28.9                                                                               29.0                                         CH.sub.3                                              347.                                                                              "                     --N∠            C.sub.14 H.sub.19 N.sub.5                                                              27.3                                                                               27.5                                         CH.sub.3                                              348.                     --NH.sub.2            C.sub.12 H.sub.17 N.sub.5                                                              30.3                                                                               31.6                349.                                                                              "                     --NH--CH.sub.3        C.sub.13 H.sub.19 N.sub.5                                                              28.6                                                                               29.0                                         CH.sub.3                                              350.                                                                              "                     --N∠            C.sub.14 H.sub.21 N.sub.5                                                              27.1                                                                               26.8                                         CH.sub.3                                              351.                                                                              --NH--NHO             --NH--CH.sub.3        C.sub.12 H.sub.17 N.sub.5                                                      O       28.4                                                                               28.6                                         CH.sub.3                                              352.                                                                              "                     --N∠            C.sub.13 H.sub.19 N.sub.5                                                      O       26.8                                                                               27.0                                         CH.sub.3                                                 CH.sub.3                                                                    353.                                                                              --NHCH.sub.2 CH.sub. 2 N∠                                                                      --NH--CH.sub.3        C.sub.12 H.sub.19 N.sub.5                                                              30.1                                                                               29.5                   CH.sub.3                                                                       C.sub.2 H.sub.5                                                             354.                                                                              --NHCH.sub.2 CH.sub.2 N∠                                                                       --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.15 H.sub.25 N.sub.5                                                      O       24.1                                                                               24.6                   C.sub.2 H.sub.5                                                                CH.sub.3                                                                    355.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              --NH--CH.sub.3        C.sub.13 H.sub.21 N.sub.5                                                              28.4                                                                               29.0                   CH.sub.3                                                                    356.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.14 H.sub.23 N.sub.5                                                      O       25.3                                                                               25.5                   C.sub.2 H.sub.5                                                             357.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                              --NH--CH.sub.3        C.sub.15 H.sub.25 N.sub.5                                                              25.5                                                                               26.0                   C.sub.2 H.sub.5                                                             358.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 --NHO                                                                 --NH--CH.sub.3        C.sub.15 H.sub.23 N.sub.5                                                      O       24.1                                                                               23.7                359.                     --NH--CH.sub.3        C.sub.16 H.sub.25 N.sub.5                                                              24.3                                                                               25.0                360.                     --NH--CH.sub.3        C.sub.15 H.sub.23 N.sub.5                                                              25.7                                                                               26.0                361.                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 --NHN--CH.sub.3                                                       --NH--CH.sub.3        C.sub.16 H.sub.26 N.sub.6                                                              27.8                                                                               27.5                362.                                                                              --NH--OH              --NH--CH.sub.3        C.sub.8 H.sub.10 N.sub.4                                                               31.5                                                                               31.9                   CH.sub.3                                                                    363.                                                                              --N∠            --NH--CH.sub.3        C.sub.10 H.sub.14 N.sub.4                                                      O       27.2                                                                               27.7                   OCH.sub.3                                                                      CH.sub.2 CH.sub.2 OH                                                        364.                                                                              --N∠            --NH--CH.sub.3        C.sub.11 H.sub.16 N.sub.4                                                      O       25.5                                                                               25.1                   OCH.sub.3                                                                   365.                     --NH--CH.sub.3        C.sub.16 H.sub.18 N.sub.4                                                      O       19.8                                                                               19.2                   CH.sub.3                                                                    366.                                                                              CH∠                                                                      CH.sub.3              --NH--CH.sub.3        C.sub.13 H.sub.20 N.sub.4                                                      O       22.6                                                                               23.0                   --N∠                                                                     OCH.sub.2 CH.sub.3                                                             H.sub.2 C                                                                      |                                                                     CH.sub.2                                                                    367.                                                                              --N∠|  --NH--CH.sub.3        C.sub.11 H.sub.14 N.sub.4                                                      O       25.6                                                                               25.6                   CH.sub.2                                                                       |                                                                     O                                                                               H.sub.2 C--CH.sub.2                                                        368.                                                                              --N∠∠CH.sub.2                                                                            --NH--CH.sub.3        C.sub.12 H.sub.16 N.sub.4                                                      O       24.1                                                                               24.5                   O--CH.sub.2                                                                 369.                                                                              --CN                  --Cl                  C.sub.8 H.sub.4 ClN.sub.3                                                              23.7                                                                               24.2                370.                                                                              --CN                  --CN                  C.sub.9 H.sub.4 N.sub.4                                                                33.3                                                                               33.8                371.                                                                              "                     --OH                  C.sub.8 H.sub.5 N.sub.3                                                                26.4                                                                               27.0                372.                                                                              "                     --OCH.sub.3           C.sub.9 H.sub.7 N.sub.3                                                                24.3                                                                               24.0                373.                                                                              "                     --NH.sub.2            C.sub.8 H.sub.6 N.sub.4                                                                35.4                                                                               35.8                374.                                                                              "                     --NH--CH.sub.3        C.sub.9 H.sub.8 N.sub.4                                                                32.6                                                                               33.0                                         CH.sub.3                                              375.                                                                              "                     --N∠            C.sub.10 H.sub.10 N.sub.4                                                              30.1                                                                               30.5                                         CH.sub.3                                                                       CH.sub.3                                              376.                                                                              "                     --N∠            C.sub.11 H.sub.12 N.sub.4                                                      O       25.9                                                                               26.4                                         CH.sub.2 CH.sub.2 OH                                  377.                                                                              --CN                                        C.sub.13 H.sub.14 N.sub.4                                                              24.8                                                                               25.2                                         CH.sub.3                                              378.                                                                              "                     --NH--N∠        C.sub.10 H.sub.11 N.sub.5                                                              34.8                                                                               35.2                                         CH.sub.3                                              379.                                                                              "                     --NH--OCH.sub.3       C.sub.9 H.sub.8 N.sub.4                                                                29.8                                                                               29.5                380.                                                                              --OCH.sub.3           --Cl                  C.sub.8 H.sub.7 ClN.sub.2                                                      O       15.4                                                                               15.0                381.                                                                              --OC.sub.2 H.sub.5    --Cl                  C.sub.9 H.sub.9 ClN.sub.2                                                      O       14.3                                                                               14.7                382.                                                                              --OC.sub.4 H.sub.9 (n)                                                                               --Cl                  C.sub.11 H.sub.13 ClN.sub.2                                                     O      12.5                                                                               12.8                383.                                                                              --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                       --Cl                  C.sub.10 H.sub.11 ClN.sub.2                                                     O      12.4                                                                               12.0                384.                                                                              --OCH.sub.3           --OCH.sub.3           C.sub.9 H.sub.10 N.sub.2                                                       O.sub.2 15.7                                                                               16.0                385.                                                                              "                     --OC.sub.2 H.sub.5    C.sub.10 H.sub.12 N.sub.2                                                      O.sub.2 14.6                                                                               14.8                386.                                                                              --OC.sub.2 H.sub.5    --OC.sub.2 H.sub.2    C.sub.11 H.sub.14 N.sub.2                                                      O.sub.2 13.6                                                                               13.9                387.                                                                              --OCH.sub.3           --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                       C.sub.11 H.sub.14 N.sub.2                                                      O.sub.3 12.6                                                                               12.2                388.                                                                              --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                       --OCH.sub.3           C.sub.11 H.sub.14 N.sub.2                                                      O.sub.3 12.6                                                                               13.0                389.                                                                              --OCH.sub.3                                 C.sub.14 H.sub.12 N.sub.2                                                      O.sub. 2                                                                               11.7                                                                               11.9                390.                                                                              "                     --SC.sub.4 H.sub.9 (n)                                                                               C.sub.12 H.sub.16 N.sub.2                                                      OS      11.9                                                                               12.1                391.                                                                              --OC.sub.2 H.sub.5    --SC.sub.2 H.sub.5    C.sub.11 H.sub.16 N.sub.2                                                      OS      12.6                                                                               13.0                392.                                                                              --OCH.sub.3                                 C.sub.14 H.sub.12 N.sub.2                                                      OS      10.9                                                                               12.1                393.                                                                              --OCH.sub.3                                 C.sub.15 H.sub.14 N.sub.2                                                      O.sub.2 11.0                                                                               11.5                394.                                                                              "                     --NH--CH.sub.3        C.sub.9 H.sub.11 N.sub.3                                                               23.7                                                                               23.5                395.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.10 H.sub.13 N.sub.3                                                      O.sub.2 20.8                                                                               21.2                396.                                                                              --OC.sub.2 H.sub.5    --NH--(CH.sub.2).sub.3 --OCH.sub.3                                                                   C.sub.13 H.sub.19 N.sub.3                                                      O.sub.2 16.9                                                                               17.3                397.                                                                              --OCH.sub.2 CH.sub.2 OCH.sub.3              C.sub.16 H.sub.17 N.sub.3                                                      O.sub.2 14.8                                                                               15.0                                         CH.sub.3                                              398.                                                                              --OC.sub.4 H.sub.9 (n)                                                                               --NH--(CH.sub.2).sub.3 --N∠                                                                    C.sub.16 H.sub.26 N.sub.4                                                      O       19.3                                                                               19.5                                         CH.sub.3                                                                       CH.sub.3                                              399.                                                                              --OCH.sub.3           --N∠            C.sub.11 H.sub.15 N.sub.3                                                      O.sub.2 19.0                                                                               19.3                                         CH.sub.2 CH.sub.2 OH                                  400.                                                                              --OC.sub.2 H.sub.5    --NHO                 C.sub.13 H.sub.16 N.sub.3                                                      O.sub.2 17.1                                                                               17.5                401.                                                                              --SCH.sub.3           --Cl                  C.sub.8 H.sub.7 ClN.sub.2                                                      S       14.1                                                                               14.5                402.                                                                              --SC.sub.2 H.sub.5    --Cl                  C.sub.9 H.sub.9 ClN.sub.2                                                      S       13.2                                                                               13.0                403.                                                                              --SC.sub.4 H.sub.9 (n)                                                                               --Cl                  C.sub.11 H.sub.13 ClN.sub.2                                                     S      11.7                                                                               12.1                404.                                                                              --SC.sub.4 H.sub.9 (n)                                                                               --OCH.sub.3           C.sub.12 H.sub.16 N.sub.2                                                      OS      11.9                                                                               12.3                405.                                                                              --SC.sub.2 H.sub.5                          C.sub.15 H.sub.14 N.sub.2                                                      OS      10.4                                                                               11.0                406.                                                                              --SC.sub.4 H.sub.9 (n)                                                                               --SC.sub.4 H.sub.9 (n)                                                                               C.sub.15 H.sub.22 N.sub.2                                                      S.sub.2  9.5                                                                               10.0                407.                                                                              --SCH.sub.3           --NH--CH.sub.3        C.sub.9 H.sub.11 N.sub.3                                                               21.7                                                                               22.0                408.                                                                              --SC.sub.2 H.sub.5    -- NH--(CH.sub.2).sub.3 --OCH.sub.3                                                                  C.sub.13 H.sub.19 N.sub.3                                                      OS      15.8                                                                               16.0                409.                                                                              --SC.sub.4 H.sub.9 (n)                                                                               --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.13 H.sub.19 N.sub.3                                                      OS      15.8                                                                               16.2                410.                                                                              "                     --NH                  C.sub.17 H.sub.19 N.sub.3                                                      S       14.1                                                                               14.5                                         CH.sub.3                                              411.                                                                              "                     --NH--(CH.sub.2).sub.3 --N∠                                                                    C.sub.16 H.sub.26 N.sub.4                                                      S       18.3                                                                               18.5                                         CH.sub.3                                                                       CH.sub.3                                              412.                                                                              "                     --N∠            C.sub.14 H.sub.21 N.sub.3                                                      OS      15.0                                                                               15.5                                         CH.sub.2 CH.sub.2 OH                                  413.                                                                              "                     --NHO                 C.sub.15 H.sub.21 N.sub.3                                                      OS      14.4                                                                               15.0                414.                                                                              --SO.sub.2 --CH.sub.3 --Cl                  C.sub.10 H.sub.10 ClN.sub.3                                                     O.sub.2 S                                                                             15.5                                                                               15.0                415.                                                                              --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                                     --Cl                  C.sub.13 H.sub.16 ClN.sub.3                                                     O.sub.2 S                                                                             13.4                                                                               13.8                416.                     --Cl                  C.sub.15 H.sub.12 ClN.sub.3                                                     O.sub.2 S                                                                             12.6                                                                               12.5                417.                                                                              -- SO.sub.2 --CH.sub.3                                                                               --CN                  C.sub.11 H.sub.10 N.sub.4                                                      O.sub.2 S                                                                              21.4                                                                               21.0                418.                                                                              "                     --OH                  C.sub.10 H.sub.11 N.sub.3                                                      O.sub.3 S                                                                              16.6                                                                               17.2                419.                                                                              "                     --OCH.sub.3           C.sub.11 H.sub.13 N.sub.3                                                      O.sub.3 S                                                                              15.7                                                                               15.3                420.                                                                              "                     --SCH.sub.3           C.sub.11 H.sub.13 N.sub.3                                                      O.sub.2 S.sub.2                                                                        14.8                                                                               15.4                421.                                                                              "                     --SO.sub.2 --CH.sub.3 C.sub.11 H.sub.13 N.sub.3                                                      O.sub.4 S.sub.2                                                                        13.3                                                                               12.9                422.                                                                              "                     --NH.sub.2            C.sub.10 H.sub.12 N.sub.4                                                      O.sub.2 S                                                                              22.2                                                                               22.6                                         CH.sub.3                                              423.                                                                              --SO.sub.2 --C.sub.2 H.sub.5                                                                         --N∠            C.sub.13 H.sub.18 N.sub.4                                                      O.sub.2 S                                                                              19.1                                                                               18.5                                         CH.sub.3                                              424.                                                                              "                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.13 H.sub.18 N.sub.4                                                      O.sub.3 S                                                                              18.1                                                                               18.7                                         CH.sub.3                                              425.                                                                              --SO.sub.2 --CH.sub.3 --N∠            C.sub.13 H.sub.18 N.sub.4                                                      O.sub.3 S                                                                              18.1                                                                               18.3                                         CH.sub.2 CH.sub.2 OH                                  426.                                                                              --SO.sub.2 --CH.sub.3 --NHO                 C.sub.14 H.sub.18 N.sub.4                                                      O.sub.3 S                                                                              17.4                                                                               17.6                                         CH.sub.3                                              427.                                                                              --SO.sub.2 --C.sub.2 H.sub.5                                                                         --NH--(CH.sub.2).sub.2 --N∠                                                                    C.sub.15 H.sub.23 N.sub.5                                                      O.sub.2 S                                                                              20.8                                                                               20.1                                         CH.sub.3                                              428.                                                                              --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                             C.sub.15 H.sub.22 N.sub.4                                                      O.sub.2 S                                                                              17.4                                                                               17.8                429.                     --NH--CH.sub.3        C.sub.17 H.sub.18 N.sub.4                                                      O.sub.2 S                                                                              16.4                                                                               16.0                430.                     --NH--CH.sub.3        C.sub.16 H.sub.16 N.sub.4                                                      O.sub.2 S                                                                              17.1                                                                               17.8                431.                                           C.sub.33 H.sub.25 N.sub.7                                                              18.9                                                                               18.5                432.                     --Cl                  C.sub.23 H.sub.20 ClN.sub.5                                                            17.5                                                                               17.9                433.                     --OCH.sub.3           C.sub.24 H.sub.23 N.sub.5                                                      O       17.6                                                                               17.0                                         CH.sub. 3                                             434.                     --N∠            C.sub.25 H.sub.26 N.sub.6                                                              20.5                                                                               21.2                                         CH.sub.3                                              435.                                                                              "                                           C.sub.37 H.sub.33 N.sub.7                                                              17.0                                                                               17.2                436.                                           C.sub.39 H.sub.37 N.sub.7                                                              16.3                                                                               16.6                437.                     --OCH.sub.3           C.sub.26 H.sub.28 N.sub.6                                                      O       19.1                                                                               19.8                438.                                                                              "                     --NH--CH.sub.3        C.sub.26 H.sub.29 N.sub.7                                                              22.3                                                                               22.5                439.                                                                              "                                           C.sub.41 H.sub.43 N.sub.9                                                              19.1                                                                               19.8                440.                                           C.sub.33 H.sub.25 N.sub.7                                                              18.9                                                                               18.1                441.                     --Cl                  C.sub.21 H.sub.15 ClN.sub.4                                                     O      15.0                                                                               15.4                442.                                                                              "                     --OC.sub.2 H.sub.5    C.sub.23 H.sub.20 N.sub.4                                                      O.sub.2 14.5                                                                               15.0                443.                                                                              "                                           C.sub.33 H.sub.23 N.sub.5                                                      O.sub.2 13.4                                                                               13.7                444.                                           C.sub.33 H.sub.23 N.sub.5                                                      S.sub.2 12.7                                                                               12.5                __________________________________________________________________________

In the following table are presented further pyridine compounds prepared in accordance with the process of this invention: ##SPC27##

or tautomeric forms.

    __________________________________________________________________________                                                    Empirical                                                                              Cal'd.                                                                             Found               No.                                                                               Y             Z.sub.1       Z.sub.2         Formula N%  N%                  __________________________________________________________________________     445.                                                                              --H           --NH.sub.2    --Cl            C.sub.6 H.sub.7 N.sub.2                                                        Cl      20.1                                                                               20.7                446.                                                                              "             "             --NH.sub.2      C.sub.6 H.sub.9 N.sub.3                                                                34.1                                                                               33.6                447.                                                                              "             "             --OH            C.sub.6 H.sub.8 N.sub.2                                                                22.6                                                                               22.8                448.                                                                              "             "             --OCH.sub.3     C.sub.7 H.sub.10 N.sub.2                                                               20.3                                                                               20.1                449.                                                                              "             "             --SC.sub.2 H.sub.5                                                                             C.sub.8 H.sub.12 N.sub.2                                                               16.6                                                                               17.1                450.                                                                              "             "             --SO.sub.2 --CH.sub.3                                                                          C.sub.7 H.sub.10 N.sub.2                                                       O.sub.2 S                                                                              15.0                                                                               15.2                451.                                                                              "             "             --NH--CH.sub.3  C.sub.7 H.sub.11 N.sub.3                                                               30.6                                                                               31.0                452.                                                                              "             --NH--CH.sub.3                                                                               "               C.sub.8 H.sub.13 N.sub.3                                                               27.8                                                                               28.2                453.                                                                              "             --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                       C.sub.10 H.sub.17 N.sub.3                                                      O.sub.2 19.9                                                                               20.2                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 454.                                                                              "             --N∠    --N∠      C.sub.14 H.sub.25 N.sub.3                                                              17.9                                                                               17.3                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 455.                                                                              "             --NHO         --NHO           C.sub.14 H.sub.21 N.sub.3                                                      O.sub.2 16.0                                                                               16.3                                               CH.sub.3                                        456.                                                                              "             --NHCH.sub.2 CH.sub.2 CH.sub.3                                                               --NHCH.sub.2 CH.sub.2 N∠                                                                 C.sub.13 H.sub.23 N.sub.4                                                              23.8                                                                               23.2                                               CH.sub.3                                        457.                                                                              --NH.sub.2    --NH.sub.2    --NH.sub.2      C.sub.6 H.sub.10 N.sub.4                                                               40.6                                                                               40.8                458.                                                                              "             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.8 H.sub.14 N.sub.4                                                               33.7                                                                               33.2                                 CH.sub.3      CH.sub.3                                        459.                                                                              "             --N∠    --N∠      C.sub.10 H.sub.18 N.sub.4                                                              28.9                                                                               28.7                                 CH.sub.3      CH.sub.3                                        460.                                                                              "             --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                       C.sub.10 H.sub.18 N.sub.4                                                      O.sub.2 24.8                                                                               25.1                461.                                                                              --NO          --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.8 H.sub.12 N.sub.4                                                               31.1                                                                               31.0                                 CH.sub.3      CH.sub.3                                        462.                                                                              "             --N∠    --N∠      C.sub.10 H.sub.16 N.sub.4                                                      O       26.9                                                                               26.7                                 CH.sub.3      CH.sub.3                                        463.                                                                              "             --NHO         --NHO           C.sub.14 H.sub.20 N.sub.4                                                      O.sub.3 19.2                                                                               19.5                464.                                                                              --NO.sub.2    --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.8 H.sub.12 N.sub.4                                                       O.sub.2 28.5                                                                               28.5                                 CH.sub.3      CH.sub.3                                        465.                                                                              "             --N∠    --N∠      C.sub.10 H.sub.16 N.sub.4                                                      O.sub.2 25.0                                                                               25.3                                 CH.sub.3      CH.sub.3                                        466.                                                                              "             --NHO         --NHO           C.sub.14 H.sub.20 N.sub.4                                                      O.sub.4 18.2                                                                               18.5                467.                                                                              --CH.sub.3    --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.9 H.sub.15 N.sub.3                                                               25.4                                                                               26.0                468.                                                                              --CH.sub.2 --CH.sub.3                                                                        --NH--CH.sub.3                                                                               --NH--CH.sub.2 --CH.sub.3                                                                      C.sub.11 H.sub.19 N.sub.3                                                              21.7                                                                               22.0                469.                                                                              --CH.sub.2 CH.sub.2 CN                                                                       --NH.sub.2    --NH.sub.2      C.sub.9 H.sub.12 N.sub.4                                                               31.8                                                                               32.0                470.             "             "               C.sub.15 H.sub.17 N.sub.3                                                      O       16.5                                                                               17.0                471.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.19 H.sub.26 N.sub.4                                                      O       17.2                                                                               17.5                   C.sub.2 H.sub.5                                                             472.                                                                              --CH.sub.2 CH.sub.2 N∠                                                                 "             --OCH.sub.2 CH.sub.2 =CH.sub.2                                                                 C.sub.16 H.sub.27 N.sub.3                                                      O       15.2                                                                               15.3                   C.sub.2 H.sub.5                                                             473.                                                                              --CH.sub.2 --CH=CH.sub.2                                                                     "             --NH--CH.sub.3  C.sub.11 H.sub.17 N.sub.3                                                              22.0                                                                               22.4                   CH.sub.3                                                                       |                                                                  474.                                                                              --CH.sub.2 --C=CH.sub.2                                                                      "             --SO.sub.2 CH.sub.2 CH=CH.sub.2                                                                C.sub.14 H.sub.20 N.sub.2                                                      O.sub.2 S                                                                              10.0                                                                               9.8                 475.                                                                              --C.sub.3 H.sub.7 (n)                                                                        --NHCH.sub.2 CH.sub.2 CH.sub.3                                                                               C.sub.15 H.sub.27 N.sub.3                                                              16.8                                                                               16.5                476.                                                                              --C.sub.4 H.sub.9 (n)                                                                        --NH--CH.sub.3                C.sub.17 H.sub.28 N.sub.2                                                      O       10.1                                                                               9.7                 477.                                                                              --C.sub.4 H.sub.9 (iso)                                                                      "                             C.sub.18 H.sub.24 N.sub.2                                                      O        9.9                                                                               10.2                478.                                                                              --C.sub.6 H.sub.13 (n)                                                                       --NH--CH.sub.3                C.sub.18 H.sub.24 N.sub.2                                                      O        9.9                                                                               10.4                479.             --NH--C.sub.3 H.sub.7 (iso)                                                                  --OCH.sub.2 CH.sub.2 OCH.sub.3                                                                 C.sub.19 H.sub.32 N.sub.2                                                      O        9.4                                                                                9.5                                               CH.sub.3                                        480.             --NH--CH.sub. 3                                                                              --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                        C.sub.19 H.sub.27 N.sub.4                                                              18.0                                                                               18.3                                               CH.sub.3                                                                       CH.sub.3                                                                       |                                      481.             --NH.sub.2    --O--CH.sub.2 --C=CH.sub.2                                                                     C.sub.16 H.sub.18 N.sub.2                                                      O       11.0                                                                               10.5                                               CH.sub.3                                        482.             "             --S--CH∠  C.sub.16 H.sub.20 N.sub.2                                                      OS       9.7                                                                                9.5                                               CH.sub.3                                        483.             --NH--CH.sub.3                C.sub.20 H.sub.19 ClN.sub.2                                                     S       7.9                                                                                8.3                484.             "                             C.sub.21 H.sub.20 Cl.sub.2                                                     N.sub.2 S                                                                               6.9                                                                                6.8                485.                                                                              --CH.sub.2 CH.sub.2 --NHO                                                                    --NH.sub.2    --NH.sub.2      C.sub.12 H.sub.20 N.sub.4                                                      O       23.7                                                                               23.9                                 CH.sub.3      CH.sub.3                                        486.                                                                              "             --N∠    --N∠      C.sub.16 H.sub.28 N.sub.4                                                      O       19.2                                                                               19.7                                 CH.sub. 3     CH.sub.3                                        487.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.15 H.sub.26 N.sub.4                                                              21.4                                                                               21.6                488.             "             "               C.sub.14 H.sub.24 N.sub.4                                                              22.6                                                                               22.2                489.                                                                              --COOCH.sub.3 "             "               C.sub.10 H.sub.15 N.sub.3                                                      O.sub.2 20.1                                                                               20.3                490.                                                                              --COOC.sub.2 H.sub.5                                                                         "             "               C.sub.11 H.sub.17 N.sub.3                                                      O.sub.2 18.8                                                                               18.5                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 491.                                                                              "             --N∠    --N∠      C.sub.17 H.sub.29 N.sub.3                                                      O.sub.2 13.7                                                                               14.0                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 492.                                                                              "             --NHO         --NH--CH.sub.3  C.sub.14 H.sub.21 N.sub.3                                                      O.sub.3 15.0                                                                               14.8                493.                                                                              --COOC.sub.4 H.sub.9 (n)                                                                     --NHCH.sub.2 CH.sub.2 OH      C.sub.15 H.sub.25 N.sub.3                                                      O.sub.4 13.5                                                                               13.8                                               CH.sub.3                                        494.                                                                              --COOC.sub.6 H.sub.13 (n)                                                                    --NHCH.sub.2 CH.sub.2 CH.sub.3                                                               --NHCH.sub.2 CH.sub.2 N∠                                                                 C.sub.20 H.sub.36 N.sub.4                                                      O.sub.2 15.4                                                                               15.0                                               CH.sub.3                                        495.                                                                              --COCH.sub.3  --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.10 H.sub.15 N.sub.3                                                      O       21.7                                                                               21.5                496.                                                                              --CO--CH=CH.sub.2                                                                            "             "               C.sub.11 H.sub.15 N.sub.3                                                      O       20.5                                                                               20.7                                               CH.sub.3                                        497.                                                                              --CO--C.sub.6 H.sub.13 (n)                                                                   --NH--CH.sub.3                                                                               --N∠      C.sub.16 H.sub.27 N.sub.3                                                      O       15.2                                                                               15.3                                               CH.sub.3                                        498.             "             "               C.sub.16 H.sub.25 N.sub.3                                                      O       15.3                                                                               15.5                499.             "             --NH--CH.sub.3  C.sub.16 H.sub.19 N.sub.3                                                      O       15.6                                                                               15.8                500.             --NH.sub.2    --NH.sub.2      C.sub.13 H.sub.13 N.sub.3                                                      O       18.5                                                                               18.3                501.                                                                              "             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.15 H.sub.17 N.sub.3                                                      O       16.5                                                                               16.7                                 CH.sub.3      CH.sub.3                                        502.                                                                              "             --N∠    --N∠      C.sub.17 H.sub.21 N.sub.3                                                      O       14.8                                                                               14.6                                 CH.sub.3      CH.sub.3                                        503.                                                                              "             --NH--CH.sub.3                                                                               --NHO           C.sub.18 H.sub.21 N.sub.3                                                      O.sub.2 13.5                                                                               13.2                504.                                                                              --CO--NH.sub.2                                                                               --NH.sub.2    --Cl            C.sub.7 H.sub.8 ClN.sub.3                                                      O       22.6                                                                               22.8                505.                                                                              "             "             --NH.sub.2      C.sub.7 H.sub.10 N.sub.4                                                               33.8                                                                               34.2                506.                                                                              --CO--NH.sub.2                                                                               --NH.sub.2    --OH            C.sub.7 H.sub.9 N.sub.3                                                        O.sub.2 25.1                                                                               24.7                507.                                                                              --CO--NH.sub.2                                                                               --NH.sub.2    --OC.sub.2 H.sub.5                                                                             C.sub.9 H.sub.13 N.sub.3                                                       O.sub.2 21.5                                                                               22.1                508.                                                                              "             "             --SC.sub.2 H.sub.5                                                                             C.sub.9 H.sub.13 N.sub.3                                                       OS      19.9                                                                               19.6                509.                                                                              "             "             --SO.sub.2 C.sub.2 H.sub.5                                                                     C.sub.9 H.sub.13 N.sub.3                                                       O.sub.3 S                                                                              17.3                                                                               17.5                510.                                                                              "             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.9 H.sub.14 N.sub.4                                                               28.9                                                                               28.7                511.                                                                              "             --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                              C.sub.13 H.sub.22 N.sub.4                                                      O.sub.3 19.9                                                                               19.6                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 512.                                                                              "             --N∠    --N∠      C.sub.15 H.sub.26 N.sub.4                                                      O       20.1                                                                               20.5                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 513.                                                                              "             --NHCH.sub.2 CH.sub.3                                                                        --NHO           C.sub.13 H.sub.20 N.sub.4                                                      O.sub.2 21.2                                                                               21.4                                               CH.sub.3                                        514.                                                                              "             "             --NHCH.sub.2 CH.sub.2 CH.sub.2 N∠                                                        C.sub.14 H.sub.25 N.sub.5                                                      O       25.1                                                                               25.3                                               CH.sub.3                                        515.                                                                              --CO--NH--CH.sub.3                                                                           --NH.sub.2    --NH.sub.2      C.sub.8 H.sub.12 N.sub.4                                                               31.1                                                                               31.0                516.                                                                              --CONHCH.sub.2 CH.sub.2 OH                                                                   --NH.sub.2    --S--CH.sub.2 --CH=CH.sub.2                                                                    C.sub.12 H.sub.17 N.sub.3                                                      O.sub.3 16.7                                                                               17.0                517.                                                                              --CONHC.sub.4 H.sub.9 (n)                                                                    --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.13 H.sub.22 N.sub.4                                                      O       22.4                                                                               22.1                   CH.sub.2                                                                    518.                                                                              --CO--N∠|                                                                     --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                              --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                C.sub. 15 H.sub.24 N.sub.4                                                     O.sub.3 18.2                                                                               18.6                   CH.sub.2                                                                       C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 519.                                                                              --CO--N∠                                                                               --N∠    --N∠      C.sub.19 H.sub.34 N.sub.4                                                      O       16.8                                                                               17.1                   C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 520.                                                                              --CO--NHO     --NH--CH.sub.3                                                                               --NH--C.sub.3 H.sub.7 (iso)                                                                    C.sub.15 H.sub.24 N.sub.4                                                      O.sub.2 19.2                                                                               19.1                521.             --NH.sub.2    --NH.sub.2      C.sub.13 H.sub.14 N.sub.4                                                      O       23.2                                                                               23.6                522.                                                                              "             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.15 H.sub.18 N.sub.4                                                      O       20.7                                                                               20.9                523.             --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 DH                                                                       C.sub.19 H.sub.26 N.sub.4                                                      O.sub.3 15.7                                                                               16.2                524.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.16 H.sub.20 N.sub.4                                                      O       19.7                                                                               19.5                525.                                                                              --SO.sub.2 --CH.sub.2 --CH.sub.3                                                             "             --NH--CH.sub.2 --CH.sub.3                                                                      C.sub.11 H.sub.19 N.sub.3                                                      O.sub.3 S                                                                              15.4                                                                               15.2                526.                                                                              --SO.sub.2 --C.sub.3 H.sub.7 (n)                                                             --NH--C.sub.3 H.sub.7 (n)     C.sub.15 H.sub.27 N.sub.3                                                      O.sub.3 S                                                                              12.8                                                                               13.1                527.                                                                              --SO.sub.2 --C.sub.4 H.sub.9 (n)                                                             --NH.sub.2    --NH.sub.2      C.sub.10 H.sub.17 N.sub.3                                                      O.sub.2 S                                                                              17.3                                                                               17.6                528.                                                                              --SO.sub.2 --C.sub.4 H.sub.9 (iso)                                                           "             "               "       17.3                                                                               17.4                                               CH.sub.3                                        529.                                                                              --SO.sub.2 --C.sub.5 H.sub.11 (iso)                                                          --NH--CH.sub.3                                                                               --N∠      C.sub.14 H.sub.25 N.sub.3                                                      O.sub.2 S                                                                              14.0                                                                               14.3                                               CH.sub.3                                        530.             "             "               C.sub.15 H.sub.25 N.sub.3                                                      O.sub.2 S                                                                              13.5                                                                               14.0                531.             "             --NH--CH.sub.3  C.sub.14 H.sub.17 N.sub.3                                                      O.sub.2 S                                                                              14.4                                                                               14.2                532.             --NHCH.sub.2 CH.sub.2 OH                                                                     --NH--CH.sub.3  C.sub.15 H.sub.18 ClN.sub.3                                                     O.sub.3 S                                                                             11.8                                                                               12.2                533.             --NHO         "               C.sub.19 H.sub.25 N.sub.3                                                      O.sub.3 S                                                                              11.2                                                                               11.4                534.                                                                              --SO.sub.2 --NH.sub.2                                                                        --NH.sub.2    --NH.sub.2      C.sub.6 H.sub.10 N.sub.4                                                       O.sub.2 S                                                                              27.7                                                                               27.5                535.                                                                              --SO.sub.2 --NH.sub.2                                                                        --NH.sub.2                    C.sub.12 H.sub.13 N.sub.3                                                      O.sub.4 S.sub.2                                                                        12.8                                                                               13.2                536.                                                                              "             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.8 H.sub.14 N.sub.4                                                       O.sub.2 S                                                                              24.4                                                                               24.2                537.                                                                              "             --NHCH.sub.2 CH.sub.2 OH                                                                     --NHCH.sub.2 CH.sub.2 OH                                                                       C.sub.10 H.sub.18 N.sub.4                                                      O.sub.4 S                                                                              19.3                                                                               19.5                   CH.sub.3                                                                    538.                                                                              --SO.sub.2 --N∠                       C.sub.20 H.sub.22 N.sub.4                                                      O.sub.2 S                                                                              14.7                                                                               15.2                   CH.sub.3                                                                    539.                                                                              --SO.sub.2 NHC.sub.2 H.sub.5                                                                 --NH--CH.sub.3                C.sub.15 H.sub.25 N.sub.3                                                      O.sub.2 S.sub.2                                                                        12.2                                                                               12.4                                               CH.sub.3                                        540.                                                                              --SO.sub.2 NH(CH.sub.2 ).sub.3 OCH.sub.3                                                     --NH.sub.2    --NH--N∠  C.sub.12 H.sub.23 N.sub.5                                                      O.sub.3 S                                                                              22.1                                                                               22.5                                               CH.sub.3                                        541.                                                                              --SO.sub.2 --NHO                                                                             "             --NH.sub.2      C.sub.10 H.sub.16 N.sub.4                                                      O.sub.3 S                                                                              20.6                                                                               21.1                542.                                                                              "             --NH--CH.sub.3                                                                               --NHO           C.sub.15 H.sub.24 N.sub.4                                                      O.sub.4 S                                                                              15.7                                                                               16.0                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 543.                                                                              "             --N∠    --N∠      C.sub.18 H.sub.32 N.sub.4                                                      O.sub.3 S                                                                              14.6                                                                               14.8                                 C.sub.2 H.sub.5                                                                              C.sub.2 H.sub.5                                 544.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.13 H.sub.22 N.sub.4                                                      O.sub.2 S                                                                              18.8                                                                               18.5                545.                                                                              "             "                             C.sub.19 H.sub.25 N.sub.3                                                      O.sub.2 S.sub.2                                                                        10.7                                                                               11.2                546.                                                                              --SO.sub.2 --NHN--CH.sub.3                                                                   "             --NH--CH.sub.3  C.sub.12 H.sub.23 N.sub.5                                                      O.sub.2 S                                                                              23.2                                                                               23.0                547.             "             "               C.sub.14 H.sub.24 N.sub.4                                                      O.sub.2 S                                                                              17.9                                                                               18.2                548.                                                                              "             "                             C.sub.19 H.sub.31 N.sub.3                                                      O.sub.4 S.sub.2                                                                         9.8                                                                               10.2                549.             --NHO         --NHCH.sub.2 CH.sub.2 OH                                                                       C.sub.19 H.sub.26 N.sub.4                                                      O.sub.4 S                                                                              13.8                                                                               13.5                550.             --NH.sub.2    --NH.sub.2      C.sub.12 H.sub.14 N.sub.4                                                      O.sub.2 S                                                                              20.1                                                                               20.3                551.                                                                              "                                           C.sub.24 H.sub.34 N.sub.4                                                      O.sub.2 S                                                                              12.7                                                                               12.5                552.                                                                              "                                           C.sub.26 H.sub.26 N.sub.4                                                      O.sub.2 S                                                                              12.2                                                                               12.5                553.                                           C.sub.24 H.sub.22 N.sub.4                                                      O.sub.2 S                                                                              13.0                                                                               13.2                554.                                                                              "                                           C.sub.32 H.sub.26 N.sub.4                                                      O.sub.2 S                                                                              10.6                                                                               10.2                                               CH.sub.3                                                                       |                                      555.                                                                              HC-- ----CH   --NH--CH.sub.3                                                                               --OCH.sub.2 C= CH.sub.2                                                                        C.sub.16 H.sub.18 N.sub.2                                                      O.sub.3  9.8                                                                                9.5                   ∥∥                                                           --OC--CCH                                                                      ∠                                                                        O                                                                                                          CH.sub.3                                        556.                                                                              "             "             --NH(CH.sub.2).sub.3 --N∠                                                                C.sub.17 H.sub.24 N.sub.4                                                      O.sub.2 17.8                                                                               18.2                                               CH.sub.3                                        557.                                                                              HC------CH    "                             C.sub.19 H.sub.24 N.sub.2                                                      O.sub.3  8.5                                                                                9.0                   ∥∥                                                           --OC--CCH                                                                      ∠                                                                        S                                                                           558.             --NH.sub.2    --NH.sub.2      C.sub.12 H.sub.12 N.sub.4                                                      O       24.5                                                                               25.0                559.                                                                              "             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.14 H.sub.16 N.sub.4                                                      O       21.8                                                                               22.2                                 CH.sub.3      CH.sub.3                                        560.                                                                              "             --N∠    --N∠      C.sub.16 H.sub.20 N.sub.4                                                      O       19.7                                                                               20.1                                 CH.sub.3      CH.sub.3                                        561.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.16 H.sub.17 N.sub.5                                                      O       23.7                                                                               23.5                                 CH.sub.3      CH.sub.3                                        562.                                                                              "             --N∠    --N∠      C.sub.18 H.sub.21 N.sub.5                                                      O       21.7                                                                               21.5                                 CH.sub.3      CH.sub.3                                        563.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.16 H.sub.16 N.sub.4                                                      OS      17.9                                                                               18.2                                 CH.sub.3      CH.sub.3                                        564.             --N∠    --N∠      C.sub.19 H.sub.22 N.sub.4                                                      O.sub.2 S                                                                              15.1                                                                               15.5                                 CH.sub.3      CH.sub.3                                        565.                                                                              HC------C--CH.sub.3                                                                          --NH--CH.sub.3                                                   ∥∥                        C.sub.20 H.sub.19 ClN.sub.2                                                     O.sub.2 S                                                                              7.3                                                                               7.0                    --OC--CCH                                                                      ∠                                                                        S                                                                           566.             --NH--CH.sub.3                                                                               --NH--CH.sub.3  C.sub.14 H.sub.18 N.sub.4                                                              23.1                                                                               23.5                567.             "             "               "       23.1                                                                               23.3                568.             "             "               C.sub.15 H.sub.20 N.sub.4                                                              21.9                                                                               21.7                                               CH.sub.3                                        569.                                                                              --C.sub.4 H.sub.9 (n)                                                                        --CN          --N∠      C.sub.13 H.sub.19 N.sub.3                                                              19.4                                                                               19.0                                               CH.sub.3                                        570.                                                                              --CO--NH.sub.2                                                                               --OCH.sub.3   --OCH.sub.3     C.sub.9 H.sub.12 N.sub.2                                                       O.sub.3 14.3                                                                               14.7                571.                                                                              --CO--CH.sub.3                                                                               --OC.sub.2 H.sub.5                                                                           --OC.sub.2 H.sub.5                                                                             C.sub.12 H.sub.17 NO.sub.3                                                              6.7                                                                                6.5                __________________________________________________________________________

In the following table are presented further pyridine compounds prepared in accordance with the method of this invention: ##SPC28##

or tautomeric forms.

    __________________________________________________________________________                                               Empirical                                                                            Cal'd.                                                                             Found                      No.                                                                               Y              Z.sub.1      Z.sub.2    Formula                                                                              N%  N%                         __________________________________________________________________________     572.                                                                              --H            --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.8 H.sub.10 N.sub.4                                                             34.6                                                                               25.0                       573.                                                                              --H            --NH--CH.sub.2 CH.sub.2 --OH                                                                           C.sub.10 H.sub.14 N.sub.4                                                      O.sub.2                                                                              25.2                                                                               25.0                                                      CH.sub.3                                        574.                                                                              --C.sub.3 H.sub.7 (n)                                                                         --NHCH.sub.2 CH.sub.2 CH.sub.3                                                              --NH(CH.sub.2).sub.3 N∠                                                             C.sub.17 H.sub.29 N.sub.5                                                            23.1                                                                               23.3                                                      CH.sub.3                                        575.                                                                              --C.sub.3 H.sub.7 (iso)                                                                       --NHCH.sub.2 CH.sub.2 CH.sub.3                                                              --NH(CH.sub.2).sub.3 H∠                                                             C.sub.17 H.sub.29 N.sub.5                                                            23.1                                                                               22.8                                                      CH.sub.3                                        576.                                                                              --C.sub.6 H.sub.13 (n)                                                                        --NHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                               C.sub.20 H.sub.34 N.sub.4                                                      O.sub. 2                                                                             15.5                                                                               16.0                          CH.sub.3                                                                    577.                                                                              --CH.sub.2 CH.sub.2 N∠                                                                  --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.12 H.sub.19 N.sub.5                                                            30.0                                                                               30.3                          CH.sub.3                                                                       CO--CH.sub.3                                                                578.                                                                              --CH.sub.2 CH.sub.2 N∠                                                                  --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.13 H.sub.19 N.sub.5                                                            26.8                                                                               27.0                       579.                                                                              --CH.sub.2 CH.sub.2 --NHO                                                                     --NH.sub.2   --NH.sub.2 C.sub.12 H.sub.17 N.sub.5                                                            28.3                                                                               28.8                       580.              --NH.sub.2   --NH.sub.2 C.sub.12 H.sub.17 N.sub.5                                                            30.3                                                                               30.5                       581.                                                                              --CH.sub.2 CH.sub.2 OH                                                                        --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.10 H.sub.14 N.sub.4                                                            27.2                                                                               27.5                       582.                                                                              --CH.sub.2 CH.sub.2 O--COCH.sub.3                                                             --NHCH.sub.2 CH.sub.2 CH.sub.2 OH                                                                      C.sub.16 H.sub.24 N.sub.4                                                      O.sub.4                                                                              16.7                                                                               17.0                       583.                                                                              --(CH.sub.2 ).sub.2 O--CONHC.sub.2 H.sub.5                                                    --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.13 H.sub.19 N.sub.5                                                      O.sub.2                                                                              25.3                                                                               25.1                       584.              --NH(CH.sub.2).sub.3 O--C.sub.3 H.sub.7 (iso)                                                          C.sub.26 H.sub.38 N.sub.4                                                      O.sub.3                                                                              12.3                                                                               12.7                       585.              --NH.sub.2   --NH.sub.2 C.sub.12 H.sub.16 N.sub.4                                                            25.9                                                                               25.5                       586.              --NH.sub.2   --NH.sub.2 C.sub.13 H.sub.12 N.sub.4                                                            25.0                                                                               25.3                       587.              --HNO        --NH--CH.sub.3                                                                            C.sub.17 H.sub.18 N.sub.4                                                            20.1                                                                               20.7                       588.              --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.14 H.sub.13 N.sub.4                                                            20.6                                                                               21.0                       589.              --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.16 H.sub.18 N.sub.4                                                            21.0                                                                               20.4                       590.                                                                              HC----CH       --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.12 H.sub.12 N.sub. 4                                                           24.5                                                                               24.7                          ∥∥                                                           --CCH                                                                          ∠                                                                        O                                                                           591.                                                                              HC----CH       --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.12 H.sub.12 N.sub.4                                                            22.9                                                                               22.5                          ∥∥                                                           --CCH                                                                          ∠                                                                        S                                                                           592.                                                                              N----CH        --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.11 H.sub.11 N.sub.5                                                            28.6                                                                               28.5                          ∥∥                                                           --CCH                                                                          ∠                                                                        S                                                                           593.              --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.14 H.sub.15 N.sub.5                                                            27.7                                                                               28.2                       594.              --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.13 H.sub.13 N.sub.5                                                            28.3                                                                               28.7                       595.              --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.15 H.sub.14 N.sub.6                                                            30.2                                                                               29.6                          N--CH                                                                       596.                                                                              --H.sub.2 C--C∠∥                                                               --NH--CH.sub.3                                                                              --NH--CH.sub.3                                                                            C.sub.12 H.sub.13 N.sub.5                                                            27.0                                                                               27.3                          S --CH                                                                      597.              --NH--C.sub.2 H.sub.5                                                                       --NH--C.sub.2 H.sub.5                                                                     C.sub.17 H.sub.18 N.sub.6                                                            27.5                                                                               27.7                                                      CH.sub.3                                        598.                                                                              --C.sub.3 H.sub.7 (n)                                                                         --CN         --N∠ C.sub.12 H.sub.14 N.sub.4                                                            26.2                                                                               26.5                                                      CH.sub.3                                        599.                                                                              --C.sub.3 H.sub.7 (n)                                                                         --SCH.sub.3  --OCH.sub.3                                                                               C.sub.11 H.sub.14 N.sub.2                                                            12.6                                                                               13.0                       __________________________________________________________________________

In the following table are presented further pyridine compounds prepared in accordance with the method of this invention: ##SPC29##

or tautomeric forms

                                                    Empirical                                                                             Cal'd.                                                                             Found               No.                                                                               X             Y         Z.sub.1   Z.sub.2    Formula                                                                               N%  N%                  __________________________________________________________________________                                          CH.sub.3                                  600.                                                                              --C.sub.3 H.sub.7 (n)                                                                        --C.sub.4 H.sub.9 (n)                                                                    --CN      --N∠ C.sub.15 H.sub.23                                                                     17.1b.3                                                                            17.5                                                     CH.sub.3                                  601.                                                                              --C.sub.3 H.sub.7 (n)                                                                        --CN      --OCH.sub.3                                                                              "          C.sub.12 H.sub.17 N.sub.3                                                      O      18.7                                                                               19.2                602.                                                                              --C.sub.3 H.sub.7 (n)                                                                        --C.sub.3 H.sub.7 (n)                                                                    --SCH.sub.3                                                                              --SCH.sub.3                                                                               C.sub.13 H.sub.21                                                              NS.sub.2                                                                              5.5 5.8                 603.                                                                              H             --CH.sub.3                                                                               --NH.sub.2                                                                               --NH.sub.2 C.sub.6 H.sub.9 N.sub.3                                                               34.1                                                                               34.5                604.                                                                              H                       --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                            C.sub.13 H.sub.16                                                                     24.5b.4                                                                            24.2                                           CH.sub.3  CH.sub.3                                  605.                                                                              H             --CO--NH.sub.2                                                                           --N∠                                                                               --N∠ C.sub.10 H.sub.16 N.sub.                                                       4 O    26.9                                                                               27.3                                           CH.sub.3  CH.sub.3                                                                       CH.sub.3                                                                       |                                606.                                                                              --C.sub.2 H.sub.5                                                                            --NH.sub.2                                                                               --NH--CH.sub.3                                                                           --OCH.sub.2 C=CH.sub.2                                                                    C.sub.12 H.sub.19 N.sub.3                                                      O      19.0                                                                               19.2                607.                                                                              --C.sub.2 H.sub.5                                                                            --H       --NHCH.sub.2 CH.sub.2 OH                                                                 --NHO      C.sub.13 H.sub.21 N.sub.3                                                      O      17.9                                                                               18.2                608.                                                                              --C.sub.4 H.sub.9 (n)                                                                        --NO      --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                            C.sub.11 H.sub.18 N.sub.4                                                      O      25.2                                                                               25.0                609.                                                                              --C.sub.4 H.sub.9 (n)                                                                        --NO.sub.2                                                                               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                            C.sub.11 H.sub.18 N.sub.4                                                      O.sub.2                                                                               23.5                                                                               23.2                610.                                                                              --C.sub.4 H.sub.9 (n)                                                                        --C.sub.4 H.sub.9 (n)                                                                    --NH.sub.2           C.sub.20 H.sub.28 N.sub.2                                                      O.sub.2                                                                               8.5 8.2                 611.                                                                              --C.sub.4 H.sub.9 (sec) --NH--C.sub.2 H.sub.5                                                                               C.sub.19 H.sub.28                                                                     17.9b.4                                                                            17.6                                 N----CH   C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                           612.                                                                              --C.sub.4 H.sub.9 (sec)                                                                      ∥∥                                                                     --N∠                                                                               --N∠ C.sub.20 H.sub.32 N.sub.4                                                      S      15.5                                                                               16.1                                 --CCH     C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                            ∠                                                                        S                                                             613.                                                                              --C.sub.4 H.sub.9 (iso) --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                     C.sub.21 H.sub.30 N.sub.4                                                      O.sub.3                                                                               14.5                                                                               14.2                614.                                                                              --C.sub.4 H.sub.9 (tert)                                                                     --CO--NH.sub.2                                                                           --NH--CH.sub.3                                                                           --SO.sub.2 CH.sub.2 CH.sub.2                                                   OCH.sub.3  C.sub.14 H.sub.23 N.sub.3                                                      O.sub.4 S                                                                             12.8                                                                               12.2                615.                                                                              --C.sub.5 H.sub.11 (iso)                                                                     --CO--NH.sub.2                                                                           --NH--CH.sub.3       C.sub.19 H.sub.22 N.sub.4                                                      O.sub.3 S                                                                             14.5                                                                               14.3                                                     CH.sub.3                                  616.                                                                              --CH=CH.sub.2 --COOC.sub.2 H.sub.5                                                                     --NHO     --N∠ C.sub.16 H.sub.23 N.sub.3                                                      O.sub.3                                                                               13.8                                                                               14.2                                                     CH.sub.3                                  617.                                                                              --CH=CH--CH.sub.3                                                                            --SO.sub.2 NH.sub.2            C.sub.20 H.sub.20 N.sub.4                                                      O.sub.2 S                                                                             14.7                                                                               15.2                   C.sub.2 H.sub.5                                                             618.                                                                              --CH.sub.2 CH.sub.2 N∠                                                                 --CH.sub.3                                                                               --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                            C.sub.14 H.sub.26                                                                     22.4b.4                                                                            22.8                   C.sub.2 H.sub.5                                                                              CH.sub.3                                                      619.                                                                              --CH.sub.2 CH.sub.2 CN                                                                       --CH.sub.2 CH.sub.2 N∠                                                             --NHO     --NH--CH.sub.3                                                                            C.sub.17 H.sub.27 N.sub.5                                                      O      22.1                                                                               22.5                                 CH.sub.3                                                      620.                                                                              --CH.sub.2 CH.sub.2 OCH.sub.3                                                                --CO--CH.sub.3                                                                           --NHCH.sub.2 CH.sub.2 CH.sub.3                                                           --SCH.sub.2 CH.sub.2 OCH.sub.3                                                            C.sub.16 H.sub.26 N.sub.2                                                      O.sub.3 S                                                                             8.6 8.9                 621.             --H       --NH(CH.sub.2).sub.3 --OCH.sub.3                                                         --NH(CH.sub.2).sub.3 --OCH.sub.3                                                          C.sub.20 H.sub.36 N.sub.4                                                      O.sub.2                                                                               15.4                                                                               15.6                                                     C.sub.2 H.sub.5                           622.             --CO--NH.sub.2      --N∠ C.sub.21 H.sub.37 N.sub.5                                                      O      18.7                                                                               18.5                                                     C.sub.2 H.sub.5                           623.             --CH.sub.2 --OCH.sub.3                                                                   --NH.sub.2                                                                               --NH.sub.2 C.sub.13 H.sub. 21                                                             N.sub.3 O                                                                             17.9                                                                               17.6                624.             --H                            C.sub.23 H.sub.19                                                                     12.5b.3                                                                            12.7                                           CH.sub.3                                            625.                                                                              "             --CO--NH.sub.2                                                                           --N∠           C.sub.22 H.sub.23 N.sub.3                                                      O.sub.3 S                                                                             10.3                                                                               10.7                                           CH.sub.3                                            626.                                                                              "             --CO--CH.sub.3                                                                           "                    C.sub.23 H.sub.21 N.sub.3                                                      O.sub.2 S                                                                             10.4                                                                               10.6                627.             --H       --NH--CH.sub.3                                                                           --NH--CH.sub.3                                                                            C.sub.12 H.sub.14                                                                     26.2b.4                                                                            26.8                                           CH.sub.3  CH.sub.3                                  628.                                                                              "             --CO--NH.sub.2                                                                           --N∠                                                                               --N∠ C.sub.15 H.sub.19 N.sub.5                                                      O      24.6                                                                               25.0                                           CH.sub.3  CH.sub.3                                  629.                                                                              N----CH       --CO--NH.sub.2                                                                           --NHCH.sub.2 CH.sub.2 OCH.sub.3                                                                     C.sub.15 H.sub.21 N.sub.5                                                      O.sub.3 S                                                                             20.0                                                                               20.3                   ∥∥                                                           --CCH                                                                          ∠                                                                         S                                                                          630.             --CO--NH.sub.2                                                                           --NH.sub.2                                                                               --OH       C.sub.13 H.sub.10 N.sub.4                                                      O.sub.2 S                                                                             19.6                                                                               19.4                __________________________________________________________________________

In those instances in the foregoing tables where only one value is presented for Z₁ and Z₂, this means that Z₁ and Z₂ are equal.

EXAMPLE 13

There are allowed to run 100 p.b.w. 3-methoxypropylamine into a suspension of 93.0 p.b.w. of 2,6-dichloro-3-cyano-4-methylpyridine in 200 p.b.w. ethyl alcohol for 2 hours at 20°C. This product is then agitated at room temperature for 18 hours. Then the resulting 2-chloro-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine of the formula ##SPC30##

is drawn off, washed on the suction apparatus first with 120 p.b.w. ethyl alcohol and subsequently with water. The substance is analytically pure.

Analysis: C₁₁ H₁₄ ClN₃ O. Calculated: 17.6% N 14.6% Cl. Found: 17.9% N 14.4% Cl.

EXAMPLE 14

Introduced into 1000 parts by weight methyl alcohol during cooling are 25.3 p.b.w. sodium. Added to this sodium methylate solution are 215 p.b.w. 2-chloro-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine, and subsequently the reaction solution is heated to the point of boiling for 24 hours under reflux. Then the methyl alcohol is distilled off and the residue stirred with water. The resulting 2-methoxy-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine of the formula ##SPC31##

is an oil, which is isolated with ether. It may be purified by vacuum distillation.

Analysis: C₁₂ H₁₇ N₃ O₂. Calculated: 17.9% N 26.4% -OCH₃. Found: 18.1% N 26.1% -OCH₃.

EXAMPLE 15

a. 13.8 p.b.w. 4-nitraniline are diazotized at 0° to +5°C. in 300 p.b.w. of water to which 36.0 p.b.w. hydrochloric acid of 30 % have been added, with a solution consisting of 7.7 p.b.w. sodium nitrite in 50 p.b.w. of water. The filtered diazo solution is allowed to run into a solution of 500 p.b.w. of water, 25.0 p.b.w. hydrochloric acid of 30 % and 32.2 p.b.w. 2.6-bis-(3'-methoxy-n.propylamino)-3-cyano-4-methyl-pyridine, whereby the reaction temperature is maintained during the coupling at 0° to +5°C. by the addition of 500 parts of ice. The pH valve of the batch is neutralized by the introduction of a solution of 65.2 p.b.w. sodium acetate in 200 p.b.w. of water, whereupon the coupling is quickly completed. The dyestuff being formed is then sucked off, washed with water until neutral and dried.

b. 1.0 g. of the dyestuff thus obtained which has the following formula ##SPC32##

is finely dispersed and introduced while stirring into 2000 g. of water. This reaction mixture is adjusted to a pH value of 5 - 6 by the addition of acetic acid and then admixed with 4 g. ammonium sulfate and 2 g. of a commercial dispersing agent on the basis of a naphthalenesulfonic acid/formaldehyde condensation product. 100 g. of a polyester fabric on the basis of polyethylene glycolterephthalate are introduced into the dye liquor thus obtained and dyed for 11/2 hours at 130°C. After subsequent rinsing, reductive aftertreatment with an alkaline sodium dithionite solution of 0.2 % during 15 minutes at 60° - 70°C., rinsing and drying, one obtains a deep reddish orange dyeing which shows very good fastness properties.

EXAMPLE 16

a. 16.3 p.b.w. 2-cyano-4-nitraniline are diazotized at 15°C. in 100 p.b.w. glacial acetic acid, with 34.2 p.b.w. nitrosylsulfuric acid of 41.3 %. The limpid diazo solution is then allowed to run into a suspension of 25.8 p.b.w. 2-methoxy-3-cyano-4-methyl-6-(3'-methoxy-propylamino)-pyridine and 66.0 g. sodium acetate in 160 p.b.w. ethanol. During the coupling the reaction temperature is maintained at 0° to +5°C. by cooling from the outside. When the coupling is completed, the dyestuff being formed is sucked off, washed first with ethanol, then with water and dried.

b. 30 p.b.w. of the dyestuff thus obtained (related to 1000 p.b.w. of the printing paste) which has the formula ##SPC33##

are incorporated in a finely dispersed form into a printing paste containing 45.0 p.b.w. carob bean meal, 6.0 p.b.w. 3-nitrobenzenesulfonic acid sodium and 3.0 p.b.w. citric acid. When this printing paste is applied onto a polyester fabric one obtains after printing, drying and setting on the thermosetting stenter during 45 seconds at 215°C., rinsing and working up as described in the above Example 15 b, a full reddish orange print which has very good fastness properties.

The dyestuff yields when printed into a triacete fabric and if it is employed in the form of the above printing paste and the printed fabric, after drying, is steamed for 10 minutes at a pressure of 2.5 atmospheres, rinsed, soaped, rinsed again and dried, a full reddish orange print having also very good fastness properties.

EXAMPLE 17

a. 29.7 g. 4-β-sulfatoethylsulfonyl-aniline-2-sulfonic acid are pasted up with 400 c.c. water, admixed with 25 c.c. 10 normal hydrochloric acid and diazotized by the addition of 100 c.c. 4 normal sodium dithionite solution. The reaction temperature is maintained at 0° to +3°C. by the addition of about 400 g. ice. The excess sodium, if any, is destroyed with little amidosulfonic acid and the diazo compound is added to a suspension of 14.8 g. 2.6-diamino-3-cyano-4-methyl-pyridine in 200 c.c. water to which 12.5 g. sodium bicarbonate have been added. The precipitated dyestuff is sucked off, and dried in vacuo. The reactive dye thus obtained has the following formula: ##SPC34##

b. A mixture of mercerized or alkalized cotton is printed with the following printing paste:50 g. of the above dyestuff100 g. urea370 g. hot water450 g. alginate thickener20 g. sodium bicarbonate sodium salt of the -10 g. m-nitrobenzenesulfonic acid1000 g.

The print may be fixed either by steaming at 103° to 105°C. or by dry heating. In both cases the fabric is subsequently rinsed and soaped. The full greenish yellow print thus obtained has very good fastness properties.

Cationic azo dyes suited for dyeing and printing polyacrylonitrile and modifier polyester fibers may be prepared according to the following Example:

EXAMPLE 18

a. 4.57 p.b.w. 4'aminophenacyltrimethyl-ammonium chloride are dissolved in 20 p.b.w. of water and 7 p.b.w. concentrated hydrochloric acid, and diazotized at 0° - 5°C. with 4 p.b.w. 5 normal sodium nitrite solution. When the diazoltization is completed, 3.52 p.b.w. 3-cyano-4-methyl-2.6-bis-methylamino-pyridine, dissolved in 10 p.b.w. glacial acetic acid, are added to the diazo solution and the reaction mixture is stirred at a pH value of 3 - 5 until the coupling is completed.

The dyestuff is precipitated by the addition of sodium chloride of 10 %, sucked off and dried. It has the following formula: ##SPC35##

b. 1 g. of this dyestuff is pasted up with 2.5 g. acetic acid of 50 % and dissolved in 6 l. of water. To this dye liquor 1 g. sodium acetate and 10 g. sodium sulfate are added. Subsequently, 100 g. of a pre-washed polyacrylonitrile staple fiber yarn are introduced into the dye liquor which has a temperature of 60°C. This temperature is slowly raised to 100°C. and dyeing is carried out during 1 hour at boiling temperature. Subsequently, the temperature is lowered down to 70°C., the treated fabric is rinsed and dried. One obtains a clear deep orange dyeing with a very good fastness to light and to wetting, and a high absorption capacity.

c. 1 g. of the dyestuff is pasted up with 2 g. acetic acid of 50 % and dissolved in 5 l. of water which contains 1 g. sodium acetate. 100 g. of a pre-washed fabric of acid modified polyester fiber are then introduced at 60°C., the temperature is slowly raised and dyeing is carried out during 1 hour at 115°C. The temperature is then lowered down to 70°C. and the fabric is rinsed and dried. Obtained is a deep orange dyeing having a very good fastness to light and wetting.

Acid azo dyes which are suited for dyeing wool, silk and polyamide may be prepared according to the following Example:

EXAMPLE 19

a. 27.7 p.b.w. 4'-amino-azobenzene-4-sulfonic acid are diazotized in the usual manner and coupled in a slightly acid pH range with 23.6 p.b.w. 2.6-(β-hydroxyethylamino)-3-cyano-4-methyl-pyridine. The dyestuff being formed is salted out by the addition of sodium chloride of 10 %, sucked off and dried at 60°C. in vacuo. In the form of its free acid it corresponds to the following formula: ##SPC36##

b. 1 g. of the above dyestuff is pasted up with 25 g. cold distilled water and dissolved in 975 g. boiling distilled water. The dyestuff solution is admixed with 2 g. acetic acid of 50 % and the reaction temperature is maintained at 60°C. At this temperature 100 g. of a pre-washed fabric of wool, silk or polyamide are introduced and the temperature is slowly raised to 100°C. and then maintained for 1 hour at boiling temperature. Subsequently, the temperature is lowered down to 70°C. and the fabric is rinsed and dried. Obtained is a deep yellowish red dyeing of high brilliancy and showing a very good fastness to light and to wetting. 

We claim:
 1. A compound of the formula ##SPC37##wherein X is alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl, benzyl, phenethyl, hydrogen, 2-dimethylaminoethyl, 2-diethylaminoethyl, 2-morpholinoethyl, 2-piperidinoethyl, 2-pyrrolidinoethyl, N-methyl-N'-piperazinoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-acetoxyethyl, 2-phenoxyacetoxyethyl, N-ethylcarbamoyloxyethyl, N-phenylcarbamoyloxyethyl, 2-phenoxyethyl, 3-methoxypropyl, 3-methylbenzyl, 2-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2-chloro-4-methylphenyl, 2-chlorophenyl, 4-chlorophenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2,5-dimethyl-4-chlorophenyl. ##SPC38## ##SPC39## ##EQU16## wherein R₇ is hydrogen, alkyl having 1 to 6 carbon atoms or phenyl and R₈ and R₉ taken separately are alkyl having 1 to 6 carbon atoms or phenyl and taken together with the nitrogen atom to which they are attached form a morpholino, pyrrolidino, piperidino or piperazino radical.
 2. The compound of claim 1 wherein X is alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, phenyl, benzyl, phenethyl or hydrogen; R₈ and R₉ taken separately are alkyl having 1 to 6 carbon atoms or phenyl and taken together with the nitrogen atom to which they are attached form a morpholino radical.
 3. The compound of claim 1 wherein Z₁ is the same as Z₂.
 4. The compound of claim 1 wherein X is methyl.
 5. The compound of claim 1 wherein X is methyl and Z₁ and Z₂ are ##EQU17##
 6. The compound of claim 1 wherein X is methyl and Z₁ and Z₂ are ##EQU18##
 7. The compound of claim 1 wherein X is methyl and Z₁ and Z₂ are ##EQU19##
 8. The compound of claim 1 wherein X is methyl and Z₁ and Z₂ are ##EQU20##
 9. The compound of claim 1 wherein X is methyl and Z₁ and Z₂ are ##EQU21##
 10. The compound of claim 1 wherein X is methyl and Z₁ and Z₂ are ##EQU22## 